Diphosphites having an open and a closed 2,4-methylated outer unit and use thereof in hydroformylation.

Diphosphites having an open and a closed 2,4-methylated outer unit and use thereof in hydroformylation.

The present disclosure pertains to a new synthetic method for the preparation of 3,6-dimethylhexahydrobenzofuran-2-one, a derivative of mint lactone, and an important organoleptic compound which finds use in the flavor and fragrance industries. Applicants' novel synthetic route is also applicable to other alkene compounds.

The present invention provides processes for the preparation of Tasimelteon (1), as well as processes for the preparation of intermediates of Formulas (2), (3) and (4) useful in the preparation of Tasimelteon (1).

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The present invention provides processes for the preparation of Tasimelteon (1), as well as processes for the preparation of intermediates of Formulas (2), (3) and (4) useful in the preparation of Tasimelteon (1).

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A method for producing a carbonyl compound represented by formula (1): ##STR00001##
wherein R.sup.1 is hydrogen or an organic group; R.sup.2 is hydrogen or an organic group; and R.sup.3 is hydrogen or an organic group; or two or three of R.sup.1, R.sup.2, and R.sup.3 may be linked to form a ring that may have at least one substituent, the method comprising step A of oxidizing an olefin compound represented by formula (2): ##STR00002##
wherein symbols are as defined above, by an oxidizing agent in the presence of (a) a non-alcohol organic solvent, (b) water, (c) a metal catalyst, and (d) an additive represented by the formula: MXn, wherein M is an element belonging to any one of Group 1, Group 2, Group 13, Group 14, and Group 15 in the periodic table, or NR.sub.4, wherein R is hydrogen or a C.sub.1-10 organic group; X is halogen; and n is a number of 1 to 5.

A method for producing a carbonyl compound represented by formula (1): ##STR00001##
wherein R.sup.1 is hydrogen or an organic group; R.sup.2 is hydrogen or an organic group; and R.sup.3 is hydrogen or an organic group; or two or three of R.sup.1, R.sup.2, and R.sup.3 may be linked to form a ring that may have at least one substituent, the method comprising step A of oxidizing an olefin compound represented by formula (2): ##STR00002##
wherein symbols are as defined above, by an oxidizing agent in the presence of (a) a non-alcohol organic solvent, (b) water, (c) a metal catalyst, and (d) an additive represented by the formula: MXn, wherein M is an element belonging to any one of Group 1, Group 2, Group 13, Group 14, and Group 15 in the periodic table, or NR.sub.4, wherein R is hydrogen or a C.sub.1-10 organic group; X is halogen; and n is a number of 1 to 5.

The invention relates to a process for preparing cyclic organic carbonates, characterized in that an epoxide is initially charged in the presence of CO.sub.2 and then a catalyst is added.

Disclosed is a method for preparing a material of plant origin rich in phenolic acids, including at least one metal, including: preparing a material of plant origin chosen from: aquatic plants; materials rich in tannins; materials rich in lignin; and obtaining a material of plant origin, rich in phenolic acids, in which the ratio of the intensity of the vibration band of the C═O bond of the COOH group and the intensity of each of the vibration bands the aromatic ring determined in FT-IR is between 0.5 and 4. The material of plant origin is brought into contact with an effluent including from 0.1 to 1000 mg/l of at least one metal, thus obtaining a material of plant origin rich in phenolic acids including from 1 to 30% by weight of at least one metal relative to the total weight of the material.

Disclosed is a method for preparing a material of plant origin rich in phenolic acids, including at least one metal, including: preparing a material of plant origin chosen from: aquatic plants; materials rich in tannins; materials rich in lignin; and obtaining a material of plant origin, rich in phenolic acids, in which the ratio of the intensity of the vibration band of the C═O bond of the COOH group and the intensity of each of the vibration bands the aromatic ring determined in FT-IR is between 0.5 and 4. The material of plant origin is brought into contact with an effluent including from 0.1 to 1000 mg/l of at least one metal, thus obtaining a material of plant origin rich in phenolic acids including from 1 to 30% by weight of at least one metal relative to the total weight of the material.