Process for preparing aryl ketone

Abstract

A process for preparing aryl ketones is disclosed. The process includes photo-oxidizing a compound of formula (V), (VI), (VII) or (VIII): ##STR00001##
in the presence of an oxidative system comprising at least one bromide compound to form aryl ketones. X.sub.1, X.sub.2, R.sub.1, R.sub.2, R.sub.3, L.sub.1, L.sub.2, L.sub.3, L.sub.4, t, n, m and p have the meanings as described in the specification and claims.

Claims

1. A process for preparing a compound of formula (I), (II), (III) or (IV): ##STR00044## said process comprising photo-oxidizing a corresponding compound of formula (V), (VI), (VII) or (VIII): ##STR00045## in the presence of an oxidative system comprising at least one bromide compound, wherein: X.sub.1 represents H, halo, OH or OR.sub.4; X.sub.2 represents H, OH, nitro, N(R.sub.4).sub.2, NHR.sub.4, R.sub.4, OR.sub.4, NR.sub.4OH, ONHR.sub.4, Si(R.sub.4).sub.3, OSi(R.sub.4).sub.3, P(R.sub.4).sub.2, P(O)(OR.sub.4).sub.2, P(O)(R.sub.4).sub.2, or a 5- or 6-membered nitrogen-linked heterocyclyl having one or two heteroatoms selected from N, O or S in which at least one heteroatom is N, with the proviso that when X.sub.1 represents OH, X.sub.2 is not OH or OR.sub.4; R.sub.1 and R.sub.2 independently represent alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, amino, amido, or an organic moiety comprising at least one of phosphor, oxygen, nitrogen and silicon, or R.sub.1 and R.sub.2, together with the carbon atom to which they attach, form a CO radical or a ring structure; R.sub.3 represents H, alkyl, cycloalkyl, aryl, heteroaryl, amino or amido; t represents an integer from 1 to 5; G represents H, halo, OH, nitro, N(R.sub.4).sub.2, NHR.sub.4, R.sub.4, OR.sub.4, NR.sub.4OH, ONHR.sub.4, Si(R.sub.4).sub.3, OSi(R.sub.4).sub.3, P(R.sub.4).sub.2, P(O)(OR.sub.4).sub.2, P(O)(R.sub.4).sub.2, or a 5- or 6-membered nitrogen-linked heterocyclyl having one or two heteroatoms selected from N, O or S in which at least one heteroatom is N; R.sub.4 represents alkyl or aryl; n, m and p independently represent an integer from 2 to 6; L.sub.1 represents an n-valent linking group; L.sub.2 represents an m-valent linking group; and L.sub.3 and L.sub.4 represent a p-valent linking group and can be the same or different from each other.

2. The process according to claim 1, wherein the compound of formula (II) has formula (II), (II) or (II): ##STR00046## R.sub.1, R.sub.2, G, L.sub.1 and n have the meanings given in claim 1.

3. The process according to claim 1, wherein X.sub.1 is H and X.sub.2 is OH or OR.sub.4.

4. The process according to claim 3, wherein the compound of formula (V), (VI), (VII) or (VIII) is obtained by an organic metal reaction.

5. The process according to claim 4, wherein the organic metal reaction is conducted by reacting a compound of formula (IX): ##STR00047## with a compound of formula (X):
R.sub.1C(O)R.sub.2(X) in the presence of magnesium, zinc or tin to form the compound of formula (V), wherein R.sub.1, R.sub.2, R.sub.3, and t are as defined in claim 1 and X is halo.

6. The process according to claim 1, wherein X.sub.1 is OH.

7. The process according to claim 1, wherein X.sub.1 is H and X.sub.2 is not OH or OR.sub.4.

8. The process according to claim 1, wherein R.sub.1 and R.sub.2 independently represent C.sub.1-3 alkyl or R.sub.1 and R.sub.2, together with the carbon atom to which they attach, form C.sub.3-8cycloalkyl; and G is Br or OH.

9. The process according to claim 1, wherein R.sub.3 is hydrogen.

10. The process according to claim 1, wherein the oxidative system further comprises one or more peroxides selected from hydrogen peroxide (H.sub.2O.sub.2), sodium peroxide (Na.sub.2O.sub.2), potassium peroxide (K.sub.2O.sub.2), calcium peroxide (CaO.sub.2), magnesium peroxide (MgO.sub.2), zinc peroxide (ZnO.sub.2), strontium peroxide (SrO.sub.2), organic peroxide and a combination thereof.

11. The process according to claim 1, wherein the bromide compound is selected from Br.sub.2, HBr, HOBr or M(Br).sub.k, wherein M is a metal ion selected from alkali metals or alkaline earth metals and k equals to the valency of M.

12. The process according to claim 1, wherein the oxidative system is selected from Br.sub.2, Br.sub.2/H.sub.2O.sub.2, HBr/H.sub.2O.sub.2, HBr/Cl.sub.2, bromide/acid/H.sub.2O.sub.2, bromide/chlorine gas, HBr/halogen acid, HBr/hypohalite, bromide/acid/halide salts, bromide salts/acid/H.sub.2O.sub.2 and bromide/acid/hypohalite and wherein the acid is selected from sulfuric acid, hydrochloric acid, hydrobromic acid, nitric acid, phosphoric acid, acetic acid, hydroiodic acid and any combination thereof.

13. The process according to claim 1, wherein both of X.sub.1 and X.sub.2 in the compound of formula (V), (VI), (VII) or (VIII) represent H, and G in the compound of formula (I), (II), (III) or (IV) represents H.

14. The process according to claim 13, wherein the compound of formula (I), (II), (III) or (IV) where G represents H is further reacted with a chloride, bromide or iodine compound and hydrolyzed to form the compound of formula (I), (II), (III) or (IV) where G represents OH.

15. The process according to claim 1, wherein G is halo and each of the compound of formulae (I), (II), (III) or (IV) is respectively converted to a compound of formula (I-1), (II-1), (III-1) or (IV-1) in the presence of a base: ##STR00048## wherein R.sub.1, R.sub.2, R.sub.3, L.sub.1, L.sub.2, L.sub.3 and L.sub.4, t, n, m, p are as described in claim 1.

16. The process according to claim 1, wherein the linking group of L.sub.1, L.sub.2, L.sub.3 and L.sub.4 are each independently a direct bond, amine, amido, a di-, tri- tetra- penta- or hexa-valent aliphatic or aromatic group or a di-, tri- tetra- penta- or hexa-valent organic group containing at least one S, P, O, N or Si atom.

17. The process according to claim 1, which is a one-pot process.

18. The process according to claim 1, wherein X.sub.1 is OR.sub.4.

19. The process according to claim 1, wherein X.sub.1 is halo.

Description

EXAMPLES

Example 1

Synthesis of 2-hydroxy-2-methyl-1-phenylpropan-1-one

(1) ##STR00033##

Preparation of 2-methyl-1-phenylpropan-2-ol

(2) 171 g (1 mol) of benzyl bromide was slowly added into 36.5 g (1.5 mol) of magnesium powder in 500 g of dry THF to form a first mixture. The first mixture was gently heated to 50 C. and stirred for 1 hour, and then 69.7 g (1.2 mol) of anhydrous acetone was slowly added to form a second mixture. The second mixture was heated to reflux for 8 hours. After cooling to room temperature, 1000 g of 10% hydrochloric acid was added, and the resulting mixture was extracted with 500 g of dichloromethane twice. Upon separation of the phases, the organic layer was dried with a desiccant (magnesium sulfate). A colorless liquid, 2-methyl-1-phenylpropan-2-ol, with a yield of 95% was obtained after the removal of desiccant and solvent from the organic layer.

Synthesis of 2-hydroxy-2-methyl-1-phenylpropan-1-one

(3) 111.8 g (0.7415 mol) of 2-methyl-1-phenylpropan-2-ol and 56 g (0.82 mol) of 50% hydrogen peroxide were mixed in 1000 g of dichloroethane to form a mixture. 252 g (1.5 mol) of hydrobromic acid was slowly added into the mixture under ice bath (0 C.), and then the mixture was irradiated by a visible light lamp (with a wavelength of about 400 nm) for 8 hours to form a crude product (in an organic layer). 1-bromo-2-methyl-1-phenylpropan-2-ol was produced with a yield of 95% after removing the solvent from the crude product by evaporation.

(4) Next, 600 g of water was mixed with 162 g (0.7 mol) of 1-bromo-2-methyl-1-phenylpropan-2-ol. The mixture was stirred at 100 C. for 1 hour and then cooled to room temperature. 76 g (1.11 mol) of 50% hydrogen peroxide was slowly added into the mixture under ice bath, and then the mixture was irradiated by a visible light lamp (with a wavelength of about 400 nm) for 6 hours to form a crude product (in an organic layer). After extracted the crude product with DCE and brine and evaporated to remove the solvent, 2-hydroxy-2-methyl-1-phenylpropan-1-one was produced with a yield of 82%. (bp. 102-103 C./4 mmHg)

Example 2

One-Pot Method for Synthesizing 2-hydroxy-2-methyl-1-phenylpropan-1-one

(5) ##STR00034##

(6) 112 g (0.745 mol) of 2-methyl-1-phenylpropan-2-ol and 127 g (1.86 mol) of 50% hydrogen peroxide were mixed in 1000 g of DCE to form a mixture. 63 g (0.373 mol) of hydrobromic acid was slowly added to the mixture at 60 C., and then mixture was irradiated by a visible light lamp (with a wavelength of about 400 nm) for 12 hours to form a crude product (in an organic layer). After extracted the curde product with DCE and brine and evaporated to remove the solvent, 2-hydroxy-2-methyl-1-phenylpropan-1-one was obtained with a yield of 85%. (bp. 102-103 C./4 mmHg)

Example 3

Synthesis of (1-hydroxycyclohexyl)-phenylmethanone

(7) ##STR00035##

Preparation of 1-benzylcyclohexan-1-ol

(8) 171 g (1 mol) of benzyl bromide was slowly added into 36.5 g (1.5 mol) of magnesium powder in 500 g of dry THF to form a first mixture. The first mixture was gently heated to 60 C. and stirred for 1 hour, and then 117.8 g (1.2 mol) of anhydrous cyclohexanone was slowly added to form a second mixture. The second mixture was heated to reflux for 8 hours. After cooling to room temperature, 1000 g of 10% hydrochloric acid was added, and the resulting mixture was extracted with 500 g of dichloromethane twice, Upon separation of the phases, the organic layer was dried with a desiccant (magnesium sulfate). A colorless liquid, 1-benzylcyclohexan-1-ol, with a yield of 90% was obtained after the removal of desiccant and solvent from the organic layer.

Synthesis of (1-hydroxycyclohexyl)-phenyl-methanone

(9) 141.8 g (0.745 mol) of i-benzylcyclohexan-1-ol and 56 g (0.82 mol) of 50% hydrogen peroxide were mixed in 1000 g of DCE to form a mixture. 252 g (1.5 mol) of hydrobromic acid was slowly added into the mixture under ice bath, and then the mixture was irradiated by a visible light lamp (with a wavelength of about 400 nm) for 8 hours to form a crude product. (1-hydroxycyclohexyl) benzyl bromide, was produced with a yield of 92% after removing the solvent from the crude product by evaporation.

(10) Next, 600 g of water was mixed with 188 g (0.7 mol) of (1-hydroxycyclohexyl) benzyl bromide. The mixture was stirred at 100 C. for 1 hour and then cooled to room temperature. 76 g (1.11 mol) of 50% hydrogen peroxide was slowly added into the mixture under ice bath, and then the mixture was irradiated by a visible light lamp (with a wavelength of about 400 nm) for 6 hours to form a crude product (in an organic layer). After extracted with DCE and brine and evaporated to remove the solvent, (1-hydroxycyclohexyl)-phenyl-methanone was produced with a yield of 65%. (bp. 175 C./15 mmHg)

Example 4

Synthesis of 2-methyl-1-phenylpropan-1-one

(11) ##STR00036##

(12) 53 g (0.78 mol) of 50%0 hydrogen peroxide was slowly added into a mixture of 100 g (0.745 mol) of isobutylbenzene and 251 g (1.49 mol) of hydrobromic acid in 1000 g of DCE under ice bath. The resulting mixture was irradiated by a visible light lamp (with a wavelength of about 400 nm) for 8 hours. After allowing the mixture to stand for a sufficient time to produce an organic layer and an aqueous layer separated from each other, (1-bromo-2-methylpropyl)benzene was produced with a yield of 95% by removing the solvent from the organic layer via evaporation.

(13) Next, 600 g of water was mixed with 149 g (0.7 mol) of (1-bromo-2-methylpropyl)benzene prepared as stated above. The mixture was stirred at 100 C. for 1 hour then cooled to room temperature. 76 g (1.11 mol) of 50% hydrogen peroxide was slowly added into the mixture under ice bath, and then the mixture was irradiated by a visible light lamp (with a wavelength of about 400 nm) for 6 hours to form a crude product (in an organic layer). After extracted with DCE and brine and evaporated to remove the solvent, 2-methyl-1-phenylpropan-1-one was produced with a yield of 80%. (bp. 217 C.)

Example 5

One-Pot Method for Synthesizing 2-methyl-1-phenylpropan-1-one

(14) ##STR00037##

(15) To 100 g (0.745 mol) of isobutylbenzene and 63 g (0.373 mol) of hydrobromic acid in 1000 g of DCE was slowly added 127 g (1.86 mol) of 50% hydrogen peroxide at 60 C. and the mixture was irradiated by a visible light lamp (with a wavelength of about 400 nm) for 12 hours to form a crude product (in an organic layer). After extracted with DCE and brine and evaporated to remove the solvent, 2-methyl-1-phenylpropan-1-one was obtained with a yield of 70%. (bp. 217 C.)

Example 6

One-Pot Method for Synthesizing -oxo-benzeneacetic acid methyl ester

(16) ##STR00038##

(17) To 100 g (0.667 mol) of methyl 2-phenylacetate and 33.7 g (0.2 mol) of hydrobromic acid was slowly added 68 g (1 mol) of 50% hydrogen peroxide at 60 C. The mixture was irradiated by a visible light lamp (with a wavelength of about 400 nm) for 12 hours to form a crude product (in an organic layer). After extracted with DCE and brine and evaporated to remove the solvent, -oxo-benzeneacetic acid methyl ester was obtained with a yield of 75%. (bp. 246-248 C.)

Example 7

Synthesis of 2-hydroxy-1-[4-[4-(2-hydroxy-2-methylpropyl)phenyl]phenyl]-2-methylpropan-1-one

(18) ##STR00039##

(19) Step 1: 82 g (1.2 mol) of 50% hydrogen peroxide was slowly added into a mixture of 100 g (0.55 mol) of 4,4-dimethyl-1,1-biphenyl and 370 g (2.2 mol) of hydrobromic acid in 1000 g of DCE under ice bath. The resulting mixture was irradiated by a visible light lamp (with a wavelength of about 400 nm) for 12 hours to form a crude product (in an organic layer). 4,4-bis(bromomethyl)-1,1-biphenyl was obtained with a yield of 75% after removing the solvent from the crude product by evaporation.

(20) Step 2: 340 g (1 mol) of 4,4-bis(bromomethyl)-1,1-biphenyl was slowly added into 73 g (3 mol) of magnesium powder in 1000 g of dry THF to form a first mixture. The first mixture was gently heated to 50C and stirred for 1 hour, and then 139 g (2.4 mol) of anhydrous acetone was slowly added to form a second mixture. The second mixture was heated to reflux for 8 hours. After cooling to room temperature, 1000 g of 10% hydrochloric acid was added to the second mixture, followed by extraction with 500 g of dichloromethane twice. Upon separation of the phases, the organic layer was dried with a desiccant (magnesium sulfate). A yellow solid product, 1,1-([1,1-biphenyl]-4,4-diyl)bis(2-methylpropan-2-ol), was obtained with a yield of 80% after the removal of desiccant and solvent from the organic layer.

(21) Step 3: To 222 g (0.745 mol) of 1,1-([1,1-biphenyl]-4,4-diyl)bis(2-methylpropan-2-ol) and 56 g (0.82 mol) of 50% hydrogen peroxide in 1000 g of DCE was slowly added 252 g (1.5 mol) of hydrobromic acid under ice bath. The mixture was irradiated by a visible light lamp (with a wavelength of about 400 nm) for 8 hours to form a crude product (in an organic layer). 1,1-([1,1-biphenyl]-4,4-diyl)bis(1-bromo-2-methylpropan-2-ol) was obtained with a yield of 90% after removing the solvent from the crude product by evaporation.

(22) Step 4: 1280 g of water was mixed with 319 g (0.7 mol) of 1,1-([1,1-biphenyl]-4,4-diyl)bis(l-bromo-2-methylpropan-2-ol), stirred at 100 C. for 1 hour and then cooled to room temperature. 76 g (1.11 mol) of 50% hydrogen peroxide was slowly added into the mixture under ice bath, and the mixture was irradiated by a visible light lamp (with a wavelength of about 400 nm) for 6 hours to form a crude product (in an organic layer). 2-hydroxy-1-[4-[4-(2-hydroxy-2-methylpropanoyl)phenyl]phenyl]-2-methylpropan-1-one was obtained with a yield of 70% after removing the solvent from the crude product by evaporation. (bp. 517 C.)

Example 8

Synthesis of 1,1-(oxybis(4,1-phenylene))bis(2-hydroxy-2-methylpropan-1-one)

(23) ##STR00040##

(24) Step 1: 82 g (1.2 mol) of 50% hydrogen peroxide was slowly added into a mixture of 109 g (0.55 mol) of 4,4-oxybis(methylbenzene) and 370 g (2.2 mol) of hydrobromic acid in 1000 g of DCE under ice bath. The resulting mixture was irradiated by a visible light lamp (with a wavelength of about 400 nm) for 12 hours to form a crude product (in an organic layer). 4,4-oxybis((bromomethyl)benzene) was obtained with a yield of 650% after removing the solvent from the crude product by evaporation.

(25) Step 2: 356 g (1 mol) of 4,4-oxybis((bromomethyl)benzene) was slowly added into 73 g (3 mol) of magnesium powder and 1000 g of dry THF to form a first mixture. The first mixture was gently heated to 50 C. and stirred for 1 hour, and then 139 g (2.4 mol) of anhydrous acetone was slowly added to form a second mixture. The second mixture was heated to reflux for 8 hours. After cooling to room temperature, 1000 g of 10% hydrochloric acid was added to the second mixture, followed by extraction with 500 g of dichloromethane twice. Upon separation of the phases, the organic layer was dried with a desiccant (magnesium sulfate). A yellow solid product, 1,1-(oxybis(4,1-phenylene))bis(2-methylpropan-2-ol), was obtained with a yield of 85% after the removal of desiccant and solvent from the organic layer.

(26) Step 3: To 234 g (0.745 mol) of 1,1-(oxybis(4,1-phenylene))bis(2-methylpropan-2-ol) and 56 g (0.82 mol) of 50 % hydrogen peroxide in 1000 g of DCE was slowly added 252 g (1.5 mol) of hydrobromic acid under ice bath. The mixture was irradiated by a visible light lamp (with a wavelength of about 400 nm) for 8 hours to form a crude product (in an organic layer). 1,1-(oxybis(4,1-phenylene))bis(1-bromo-2-methylpropan-2-ol) was obtained with a yield of 90% after removing the solvent from the crude product by evaporation.

(27) Step 4: 1320 g of water was mixed with 330 g (0.7 mol) of 1,1-(oxybis(4,1-phenylene))bis(1-bromo-2-methylpropan-2-ol), stirred at 100C for 1 hour and then cooled to room temperature. 76 g (1.11 mol) of 50% hydrogen peroxide was slowly added into the mixture under ice bath, and the mixture was irradiated by a visible light lamp (with a wavelength of about 400 nm) for 6 hours to form a crude product (in an organic layer). 1,1-(oxybis(4,1-phenylene))bis(2-hydroxy-2-methylpropan-1-one) was obtained with a yield of 75% after removing the solvent from the crude product by evaporation. (bp. 502-504 C.)

Example 9

Synthesis of 1,1-propane-2,2-diylbis(4,1-phenylene))bis(2-hydroxy-2-methylpropan-1-one)

(28) ##STR00041##

(29) Step 1: 82 g (1.2 mol) of 50% hydrogen peroxide was slowly added into a mixture of 123 g (0.55 mol) of 4,4-(propane-2,2-diyl)bis(methylbenzene) and 370 g (2.2 mol) of hydrobromic acid in 1000 g of DCE under ice bath. The resulting mixture was irradiated by a visible light lamp (with a wavelength of about 400 nm) for 12 hours to form a crude product (in an organic layer). 4,4-(propane-2,2-diyl)bis((bromomethyl)benzene) was obtained with a yield of 85% after removing the solvent from the crude product by evaporation.

(30) Step 2: 382 g (1 mol) of 4,4-(propane-2,2-diyl)bis((bromomethyl)benzene) was slowly added into 73 g (3 mol) of magnesium powder and 1000 g of dry THF to form a first mixture. The first mixture was gently heated to 50 C. and stirred for 1 hour, and then 139 g (2.4 mol) of anhydrous acetone was slowly added to form a second mixture. The second mixture was heated to reflux for 8 hours. After cooling to room temperature, 1000 g of 10% hydrochloric acid was added, followed by extraction with 500 g of dichloromethane twice. Upon separation of the phases, the organic layer was dried with a desiccant (magnesium sulfate). A yellow solid product, 1,1-(propane-2,2-diylbis(4,1-phenylene))bis(2-methylpropan-2-ol), was obtained with a yield of 85% after the removal of desiccant and solvent from the organic layer.

(31) Step 3: To 253 g (0.745 mol) of 1,1-(propane-2,2-diylbis(4,1-phenylene))bis(2-methylpropan-2-ol) and 56 g (0.82 mol) of 50% hydrogen peroxide in 1000 g of DCE was slowly added 252 g (1.5 mol) of hydrobromic acid under ice bath. The mixture was irradiated by a visible light lamp (with a wavelength of about 400 nm) for 8 hours to form a crude product (in an organic layer). 1,1-(propane-2,2-diylbis(4,1-phenylene))bis(1-bromo-2-methylpropan-2-ol) was obtained with a yield of 90% after removing the solvent from the crude product by evaporation.

(32) Step 4: 1396 g of water was mixed with 349 g (0.7 mol) of 1,1-(propane-2,2-diylbis(4,1-phenylene))bis(1-bromo-2-methylpropan-2-ol), stirred at 100 degree for 1 hour and then cooled to room temperature. 76 g (1.11 mol) of 50% hydrogen peroxide was slowly added into the mixture under ice bath, and the mixture was irradiated by a visible light lamp (with a wavelength of about 400 nm) for 6 hours to form a crude product (in an organic layer). 1,1-(propane-2,2-diylbis(4,1-phenylene))bis(2-hydroxy-2-methylpropan-1-one), was obtained with a yield of 85% after removing the solvent from the crude product by evaporation. (bp. 574 C.)

Example 10

Synthesis of 2-methyl-phenylpropan-1-one

(33) ##STR00042##

(34) 17.8 g (0.1 mol) of (1-ethoxy-2-methyl-propyl)benzene was mixed with 17 g (0.1 mol) of hydrobromic acid and 20 g of cyclohexane under ice bath, and 7 g (0.1 mol) of 50% hydrogen peroxide was slowly added into the mixture and then the mixture was irradiated by a visible light lamp (with a wavelength of about 400 nm) for 3 hours. The organic layer was separated from the mixture and further extracted with 10 g water. The extracted organic layer was collected and concentrated to dryness to give 12 g of 2-methyl-1-phenylpropan-1-one (yield 80%). (bp. 217 C.)

Example 11

Synthesis of phenyl-[4-(phenylcarbonyl))cyclohexyl]methanone

(35) ##STR00043##

(36) Step 1: 143 g (2.1 mol) of 50% hydrogen peroxide was slowly added into a first mixture of 264 g (1 mol) of 1,4-Dibenzylcyclohexane (from 3B Scientific Corporation), 674 g (4 mol) of hydrobromic acid and 500 g of cyclohexane under ice bath to form a second mixture, and the second mixture was irradiated by a visible light lamp (with a wavelength of about 400 nm) for 8 hours. The organic layer was separated from the aqueous layer and further extracted with 100 g water. The extracted organic layer was collected and concentrated to dryness to give 316 g of 1,4-bis(-bromobenzyl)-cyclohexane (yield: 75%).

(37) Step 2: 316 g (0.75 mol) of 1,4-bis(-bromobenzyl)-cyclohexane obtained from Step 1 and 2532 g of water were mixed and heated to reflux for 8 hours to form a third mixture. After cooling to room temperature, water was removed by filtration. The remaining solid was mixed with 250 g of cyclohexane and 126 g (0.75 mol) of hydrobromic acid under ice bath to form a fourth mixture. 106 g (1.55 mol) of 50% hydrogen peroxide was slowly added into the fourth mixture to form a fifth mixture, and the fifth mixture was irradiated by a visible light lamp (with a wavelength of about 400 nm) for 8 hours. The organic layer was separated from the aqueous layer and further extracted with 100 g water. The extracted organic layer was collected and concentrated to dryness to give 175 g of phenyl-[4-(phenyl carbonyl)cyclohexyl]methanone (yield: 80%, bp. 437 C.).

(38) The above disclosure is related to the detailed technical contents and inventive features thereof. Persons of ordinary skill in the art may proceed with a variety of modifications and replacements based on the disclosures and suggestions of the invention as described without departing from the characteristics thereof. Nevertheless, although such modifications and replacements are not fully disclosed in the above descriptions, they have substantially been covered in the following claims as appended.