Method for producing cross-coupling compound
AssigneeKao Corporation
InventorsTaketoshi Fujimori, Mio Ishita, Yoshinori Nishizawa
Life of this patent
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Abstract
To provide a method for performing a cross-coupling reaction of a Grignard compound with an alkyl halide simply, efficiently and in high yield, a method for obtaining a ω-bromo long chain carboxylic acid simply and efficiently using an easily obtainable raw material and a method for producing a useful branched fatty acid simply and efficiently [R1: an alkyl group having 1 to 15 carbon atoms, R2: an alkyl group having 1 to 30 carbon atoms with a carboxyl group and X and X′: a halogen atom] [n: an integer of 9 to 17] [n: an integer of 9 to 17, R1a: a branched alkyl group having 3 to 8 carbon atoms and X: a halogen atom].
Claims21
A method for producing cross-coupling compounds represented by:
- R1—R2
- wherein R1 represents an alkyl group having 1 to 15 carbon atoms and R2 represents an alkyl group having 1 to 30 carbon atoms with a carboxyl group, said method comprising cross-coupling a Grignard compound represented by:
- R1MgX
- wherein R1 is as defined in the above, with an alkyl halide represented by:
- R2—X′
- wherein R2 is as defined in the above, in the presence of a copper compound and a trivalent phosphoric acid compound, a crown ether compound, or a combination thereof.
A method for producing a ω-bromo long chain carboxylic acid represented by:
- Br—(CH2)n—CO2H
- wherein n represents an integer of 9 to 17, the method comprising:
- reacting a cyclic ester with hydrogen bromide in the presence of an acetic acid solvent to obtain the a ω-bromo long chain carboxylic acid;
- wherein:
- the cyclic ester is represented by formula (1):
- where n is as defined in the above;
- the reaction is carried out in a closed system;
- and
- the acetic acid solvent consists of acetic acid and optionally at least one additional solvent selected from the group consisting of tetrahydrofuran, diethyl ether, dimethyl ether, methoxyethane, 1,2-dimethoxy ethane, t-butylmethyl ether, isopropyl ether, dioxane, cyclopentylmethyl ether, hexane, cyclohexane, heptane, isooctane, decane, benzene, toluene, and xylene.
A method for producing a branched fatty acid having 13 to 26 carbon atoms represented by
- R1a—(CH2)n—CO2H
- wherein R1a represents a branched alkyl group having 3 to 8 carbon atoms and n represents an integer of 9 to 17, the method comprising:
- reacting a cyclic ester with hydrogen bromide in the presence of an acetic acid solvent to obtain a bromocarboxylic acid;
- and
- reacting the bromocarboxylic acid with a Grignard compound to obtain the branched fatty acid;
- wherein:
- the cyclic ester is represented by formula (1):
- wherein n is as defined in the above;
- the bromocarboxylic acid is represented by:
- Br—(CH2)n—CO2H
- wherein n is as defined above;
- the Grignard compound is represented by:
- R1a MgX
- wherein R1a is as defined above and X represents a halogen atom;
- the bromocarboxylic acid is free of bromocarboxylic acid ester;
- and
- the bromocarboxylic acid is reacted with the Grignard compound in the presence of a copper compound and a trivalent phosphorous compound.
A method for producing a branched fatty acid having 13 to 26 carbon atoms represented by
- R1a—(CH2)n—CO2H
- wherein R1a represents a branched alkyl group having 3 to 8 carbon atoms and n represents an integer of 9 to 17, the method comprising:
- reacting a cyclic ester with hydrogen bromide in the presence of an acetic acid solvent to obtain a bromocarboxylic acid;
- and
- reacting the bromocarboxylic acid with a Grignard compound to obtain the branched fatty acid;
- wherein:
- the cyclic ester is represented by formula (1):
- wherein n is as defined in the above;
- the bromocarboxylic acid is represented by:
- Br—(CH2)n—CO2H
- wherein n is as defined above;
- the Grignard compound is represented by:
- R1a MgX
- wherein R1a is as defined above and X represents a halogen atom;
- and
- the bromocarboxylic acid is reacted with the Grignard compound in the presence of a copper compound and a crown ether.
Dependencies are inferred from the claim text.