Process for producing chroman compound
AssigneeMitsubishi Gas Chemical Company, Inc.
InventorsKazuo Tanaka, Youichi Kyuuko, Toshio Hidaka
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Abstract
The invention provides a process for producing a chroman compound represented by formula (1), characterized in that the process includes allowing a phenol, an unsaturated compound, and a formaldehyde to react in the absence of catalyst and in the presence of water in an amount by mole 1 to 10 times that of the phenol. According to the present invention, a high-purity chroman compound can be produced in the absence of catalyst and under mild conditions. In addition, the invention provides an industrial means for producing the compound, without using a large amount of an acid or a base serving as a reaction promoter or a catalyst, which would otherwise cause side reactions, apparatus corrosion, etc.
Claims12
A process for producing a chroman compound represented by formula (1):
- [F1]
- (wherein each of substituents R1 to R4 represents a hydrogen atom, a halogen atom, a hydroxyl group, a methoxy group, an ethoxy group, a carboxyl group, a C1 to C12 alkyl group which may have a substituent, a C6 to C12 aryl group which may have a substituent, a C7 to C12 aralkyl group which may have a substituent, or an ester residue;
- R1 to R4 may be linked to one another;
- each of R5 to R6 represents a hydrogen atom or a C1 to C12 alkyl group, and X represents a hydrogen atom, a carboxyl group, an amide group, a nitrile group, an aldehyde group, an ester group and a C1 to C12 alkyl group which may have a substituent, the substituent represents a halogen atom, a hydroxyl group, a carboxyl group or an ester group, characterized in that the process comprises allowing a phenol represented by formula (2):
- (wherein each of R1 to R4 represents as same as those of formula (1)),
- an unsaturated compound represented by formula (3):
- (wherein R5;
- R6 and X represent as same as those of formula (1)) and a formaldehyde to react in the absence of catalyst and in the presence of water in an amount by mole 1 to 10 times that of the phenol.
(canceled)
A process for producing a chromancarboxylic acid ester as described in claim 12, wherein the phenol is an alkylphenol or a polyhydroxybenzene.
A process for producing a chromancarboxylic acid ester as described in claim 12, wherein the methacrylate ester and the formaldehyde are used in amounts in stoichiometrically excess of the amount of the phenol.
A process for producing a chromancarboxylic acid ester as described in claim 12, wherein the formaldehyde is at least one member selected from the group consisting of formaldehyde and paraformaldehyde.
A process for producing methyl 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylate, characterized in that the process comprises allowing 1,4-dihydroxy-2,3,5-trimethylbenzene, methyl methacrylate, and a formaldehyde to react in the absence of catalyst and in the presence of water in an amount by mole 1 to 10 times that of 1,4-dihydroxy-2,3,5-trimethylbenzene.
A process for producing a chromancarboxylic acid, characterized by comprising hydrolyzing a chromancarboxylic acid ester produced through a process as recited in claim 12.
A process for producing a chromancarboxylic acid ester represented by formula (4):
- [F4]
- (wherein each of R1 to R4 represents a hydrogen atom, a halogen atom, a hydroxyl group, a methoxy group, an ethoxy group, a carboxyl group, or a C1 to C12_alkyl group which may have a substituent, a C6 to C12 aryl group which may have a substituent, a C7 to 012 aralkyl group which may have a substituent;
- R1 to R4 may be linked to one another;
- R represents a C1 to C12 alkyl group which may have a substituent, the substituent represents a halogen atom, a hydroxyl group, a carboxyl group or an ester group), characterized in that the process comprises allowing a phenol represented by formula (2):
- [F5]
- (wherein each of substituents R1 to R4 represents as same as those of formula (4)), a methacrylate ester represented by formula (5):
- [F6]
- (wherein R represents as same as that of formula (4))
- and a formaldehyde to react in the absence of catalyst and in the presence of water in an amount by mole 1 to 10 times that of the phenol.
Dependencies are inferred from the claim text.