Method for producing chroman-carboxylic acid
AssigneeKuraray Co., Ltd.
InventorsTatsuhiko Hayashibara, Junko Sato, Masahiro Torihara
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Abstract
A method for producing a chroman-carboxylic acid is provided, which method includes reacting a dialkylphenol compound, a formaldehyde and an alcohol in the presence of a secondary amine and an acid to give an alkoxymethylated phenol compound (Step 1); reacting the obtained alkoxymethylated phenol compound with an ester having a carbon-carbon double bond at a temperature of not less than 100° C. to give a dialkylchroman carboxylic acid ester (Step 2); hydrolyzing the obtained dialkylchroman carboxylic acid ester to give a dialkylchroman-carboxylic acid (Step 3); and reacting the obtained dialkylchroman-carboxylic acid with an aromatic hydrocarbon in the presence of a Lewis acid (Step 4).
Claims19
A method for producing a chroman-carboxylic acid of the formula (II)
- wherein R3 is a hydrogen atom or an alkyl group, which method comprises reacting a dialkylchroman-carboxylic acid of the formula (I)
- wherein R1 and R2 are each independently an alkyl group and R3 is as defined above, with an aromatic hydrocarbon in the presence of a Lewis acid.
A method for producing a chroman-carboxylic acid of the formula
- wherein R3 is a hydrogen atom or an alkyl group, which method comprises reacting a dialkylphenol compound of the formula (III)
- wherein R1 and R2 are each independently an alkyl group;
- a formaldehyde, and an alcohol in the presence of a secondary amine and an acid to give an alkoxymethylated phenol compound of the formula (IV)
- wherein R1 and R2 are as defined above and R4 is an alkoxyl group;
- reacting the obtained alkoxymethylated phenol compound with an ester of the formula (V)
- wherein R3 is as defined above and R5 is an alkyl group or an aralkyl group, having a carbon-carbon double bond, at a temperature of not less than 100° C. to give a dialkylchroman carboxylic acid ester of the formula (VI)
- wherein R1, R2, R3 and R5 are as defined above;
- hydrolyzing the obtained dialkylchroman carboxylic acid ester to give dialkylchroman-carboxylic acid of the formula (I)
- wherein R1, R2 and R3 are as defined above;
- and reacting the obtained dialkylchroman-carboxylic acid with an aromatic hydrocarbon in the presence of a Lewis acid.
A dialkylchroman-carboxylic acid of the formula (I)
- wherein R1 and R2 are each independently an alkyl group and R3 is a hydrogen atom or an alkyl group.
An alkoxymethylated phenol compound of the formula (IV)
- wherein R1 and R2 are t-butyl group and R4 is an alkoxyl group.
A method for producing a dialkylchroman-carboxylic acid of the formula (I)
- wherein R1 and R2 are each independently an alkyl group and R3 is a hydrogen atom or an alkyl group, which method comprising reacting a dialkylphenol compound of the formula (III)
- wherein R1 and R2 are as defined above, a formaldehyde and an alcohol in the presence of a secondary amine and an acid to give an alkoxymethylated phenol compound of the formula (IV)
- wherein R1 and R2 are as defined above and R4 is an alkoxyl group;
- reacting the obtained alkoxymethylated phenol compound with an ester of the formula (V)
- wherein R3 is as defined above and R5 is an alkyl group or an aralkyl group, having a carbon-carbon double bond, at a temperature of not less than 100° C. to give a dialkylchroman carboxylic acid ester of the formula (VI)
- wherein R1, R2, R3 and R5 are as defined above;
- and hydrolyzing the obtained dialkylchroman carboxylic acid ester.
Dependencies are inferred from the claim text.