The present invention relates to the production of benzene derivatives from furfural and its derivatives. The present invention also relates to the preparation of novel intermediates derived from furfural and its derivatives. The present invention describes new routes for converting furfural and its derivatives into benzene derivatives including novel intermediates.

The present invention relates to the production of benzene derivatives from furfural and its derivatives. The present invention also relates to the preparation of novel intermediates derived from furfural and its derivatives. The present invention describes new routes for converting furfural and its derivatives into benzene derivatives including novel intermediates.

A process for preparing an amine by reacting an aldehyde and/or ketone with a nitrogen compound selected from the group consisting of ammonia and primary and secondary amines, and subsequent hydrogenation of the resulting reaction product in the liquid phase and in the presence of hydrogen and a heterogeneous copper oxide hydrogenation catalyst at a temperature of 20 to 230° C., wherein the aldehyde and/or ketone is reacted with the nitrogen compound either together with the hydrogenation in the liquid phase and in the presence of the hydrogen and of the catalyst (alternative 1) or in a step preceding the hydrogenation (alternative 2), and wherein the catalytically active composition of the catalyst, prior to reduction thereof with hydrogen, comprises at least 24% by weight of oxygen compounds of copper, calculated as Cu.

A process for preparing an amine by reacting an aldehyde and/or ketone with a nitrogen compound selected from the group consisting of ammonia and primary and secondary amines, and subsequent hydrogenation of the resulting reaction product in the liquid phase and in the presence of hydrogen and a heterogeneous copper oxide hydrogenation catalyst at a temperature of 20 to 230° C., wherein the aldehyde and/or ketone is reacted with the nitrogen compound either together with the hydrogenation in the liquid phase and in the presence of the hydrogen and of the catalyst (alternative 1) or in a step preceding the hydrogenation (alternative 2), and wherein the catalytically active composition of the catalyst, prior to reduction thereof with hydrogen, comprises at least 24% by weight of oxygen compounds of copper, calculated as Cu.

The present invention provides a method for chiral resolution of Trolox. The present disclosure relates to a method for producing a solid salt of a compound of formula I, wherein an amide-based solvent is added to a sample, which contains a compound of formula I, while being assumed to contain a compound of formula II, in the presence of an optical resolution agent:

##STR00001## Formula I: (R)-6-hydroxy-2, 5, 7, 8-tetramethylchroman-2-carboxylic acid (hereinafter referred to R Trolox)

##STR00002## Formula II: (S)-6-hydroxy-2, 5, 7, 8-tetramethylchroman-2-carboxylic acid (hereinafter referred to S Trolox).

Provided is an alkyldiphenylmethane protective agent, which can prevent solidification or insolubilization of a compound by protecting a functional group of the compound to achieve easy separation and purification after a reaction. An alkyldiphenylmethane compound represented by general formula (1): ##STR00001## wherein Y represents —OR.sup.19 (wherein R.sup.19 represents a hydrogen atom or an active ester-type protecting group), —NHR.sup.20 (wherein R.sup.20 represents a hydrogen atom, a C.sub.1-6 linear or branched alkyl group, or an aralkyl group), isocyanate group, an azide group, or a halogen atom, Z represents a C.sub.1-4 linear or branched alkyl group, an alkenyl group, or a cycloalkyl group, at least one of R.sup.1 to R.sup.10 represents a group represented by formula (2):
—O—R.sup.11—X-A  (2) and the others each independently represent a hydrogen atom, a halogen atom, a C.sub.1-4 alkyl group, or a C.sub.1-4 alkoxy group; R.sup.11 represents a C.sub.1-16 linear or branched alkylene group; X represents O or CONR.sup.21 (wherein R.sup.21 represents a hydrogen atom or a C.sub.1-4 alkyl group); and A represents, for example, a group represented by formula (3): ##STR00002## wherein R.sup.12, R.sup.13, and R.sup.14 may be the same or different and each independently represent a C.sub.1-6 linear or branched alkyl group or an optionally substituted aryl group; R.sup.15 represents a single bond or a C.sub.1-3 linear or branched alkylene group; and R.sup.16, R.sup.17, and R.sup.18 each independently represent a C.sub.1-3 linear or branched alkylene group.

Provided is an alkyldiphenylmethane protective agent, which can prevent solidification or insolubilization of a compound by protecting a functional group of the compound to achieve easy separation and purification after a reaction. An alkyldiphenylmethane compound represented by general formula (1): ##STR00001## wherein Y represents —OR.sup.19 (wherein R.sup.19 represents a hydrogen atom or an active ester-type protecting group), —NHR.sup.20 (wherein R.sup.20 represents a hydrogen atom, a C.sub.1-6 linear or branched alkyl group, or an aralkyl group), isocyanate group, an azide group, or a halogen atom, Z represents a C.sub.1-4 linear or branched alkyl group, an alkenyl group, or a cycloalkyl group, at least one of R.sup.1 to R.sup.10 represents a group represented by formula (2):
—O—R.sup.11—X-A  (2) and the others each independently represent a hydrogen atom, a halogen atom, a C.sub.1-4 alkyl group, or a C.sub.1-4 alkoxy group; R.sup.11 represents a C.sub.1-16 linear or branched alkylene group; X represents O or CONR.sup.21 (wherein R.sup.21 represents a hydrogen atom or a C.sub.1-4 alkyl group); and A represents, for example, a group represented by formula (3): ##STR00002## wherein R.sup.12, R.sup.13, and R.sup.14 may be the same or different and each independently represent a C.sub.1-6 linear or branched alkyl group or an optionally substituted aryl group; R.sup.15 represents a single bond or a C.sub.1-3 linear or branched alkylene group; and R.sup.16, R.sup.17, and R.sup.18 each independently represent a C.sub.1-3 linear or branched alkylene group.

The present invention provides a process for preparing 2-methyl-N-(2′-methylbutyl)butanamide of the following formula (1):the process comprising: subjecting an α-arylethyl-2-methylbutylamine compound of the following general formula (2): wherein Ar represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, to N-2-methylbutyrylation to form an N-α-arylethyl-2-methyl-N-(2′-methylbutyl)butanamide compound of the following general formula (3): wherein Ar is as defined above, and removing the α-arylethyl group of the resulting compound (3) to form 2-methyl-N-(2′-methylbutyl)butanamide (1).

##STR00001##

The present invention provides a process for preparing 2-methyl-N-(2′-methylbutyl)butanamide of the following formula (1):the process comprising: subjecting an α-arylethyl-2-methylbutylamine compound of the following general formula (2): wherein Ar represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, to N-2-methylbutyrylation to form an N-α-arylethyl-2-methyl-N-(2′-methylbutyl)butanamide compound of the following general formula (3): wherein Ar is as defined above, and removing the α-arylethyl group of the resulting compound (3) to form 2-methyl-N-(2′-methylbutyl)butanamide (1).

##STR00001##

Provided is a catalyst which comprises a compound represented by formula (1) and which exhibits activity for at least one type of reaction selected from among hydrosilylation reaction or hydrogenation reaction with respect to an aliphatic unsaturated bond and hydrosilane reduction reaction with respect to a carbon-oxygen unsaturated bond or a carbon-nitrogen unsaturated bond. Formula (1): M.sub.n(L.sub.m) {M represents Fe, Co, or Ni having an oxidation number of 0, L represents an isocyanide ligand represented by formula (2), n denotes an integer of 1-8, and m denotes an integer of 2-12. Formula (2): (CN).sub.x—R.sup.1 (R.sup.1 represents a mono- to trivalent-organic group having 1-30 carbon atoms, optionally being substituted by a halogen atom, and optionally having interposed therein one or more atoms selected from among O, N, S, and Si; and x denotes an integer of 1-3.)}.