Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1997-04-30
1998-09-15
Dentz, Bernard
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
554148, 554213, C07D30758, C07C 5901, C07C 5109
Patent
active
058081062
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/JP95/01555 filed Aug. 4, 1995.
TECHNICAL FIELD
The present invention relates to a method for producing 2-(.omega.-alkoxycarbonyl alkanoyl)-4-butanolide and a long-chain .omega.-hydroxycarboxylic acid
BACKGROUND OF THE INVENTION
A macrocyclic lactone can be derived from a long-chain .omega.-hydroxycarboxylic acid through intramolecular cyclization. Such macrocyclic lactones as cyclopentadecanolide and cyclohexadecanolide are important materials for preparing musk odor. It is known that 2-(.omega.-alkoxycarbonyl alkanoyl)-4-butanolide can be converted into a long-chain .omega.-hydroxycarboxylic acid through hydrolysis, decarboxylation, and subsequent reduction of the carbonyl group. The present invention relates to a method for producing a long-chain .omega.-hydroxycarboxylic acid, which is an intermediate to macrocyclic lactones, and 2-(.omega.-alkoxycarbonyl alkanoyl)-4-butanolide, which is an intermediate to said acid.
Conventionally, there have been many known methods to synthesize long-chain .omega.-hydroxycarboxylic acids such as 15-hydroxypentadecanoic acid and 16- hydroxyhexadecanoic. An example is the method disclosed in Dutch method, however, needs as many as ten steps to produce a long-chain .omega.-bromoxylic acid, which is hydrolyzed into a long-chain .omega.-hydroxycarboxylic acid. This cannot provide a satisfactory industrial process because of the need for many steps for synthesis, relatively low availability of material substances, and hence, unsuitability for industrial mass-production.
Another known method is disclosed in Japanese Patent Laid-Open (Kokai) HEI 5-86013, which uses a .omega.-cyano fatty ester and .gamma.-butyrolactone as starting materials. Specifically, 11-methyl cyanoundecanoate reacts .gamma.-butyrolactone in the presense of an alkali metal alcoholate to produce .alpha.-(11-cyanoundecanoyl)-.gamma.-butyrolactone, which is then hydrolyzed into 15-hydroxy-12-ketopentadecanonitrile, followed by isolation, secondary hydrolysis, and reduction to provide 15-hydroxypentadecanoic acid.
This method, though being a good one, is still not sufficiently satisfactory because many of the starting materials are not highly available and also because 11-methyl and cyanoundecanoate, which is relatively high in price, has to be used as a material. Another problem, though not very serious, is that the nitrile group at the .omega.-position has to be converted finally into a carboxyl group.
SUMMARY OF THE INVENTION
The objective of the invention is to provide an industrially advantageous method for producing 2-(.omega.-alkoxycarbonyl alkanoyl)-4-butanolide, which eventually makes it possible to produce a long-chain .omega.-hydroxycarboxylic acid through a short process and from highly available materials. Another objective is to provide an industrially advantageous method for producing a long-chain .omega.-hydroxycarboxylic acid.
The present inventors have reached the invention after earnest studies which show that 2-(.omega.-alkoxycarbonyl alkanoyl)-4-butanolide can be produced unexpectedly with a high selectivity and yield through condensation reacting of .gamma.-butyrolactone with a highly available, lo.omega.-price dicarboxylate as represented by the following general formula: ROOC(CH.sub.2).sub.n COOR (where n denotes an integer of 7 to 13, and R denotes an alkyl or an alkenyl group). The present inventors have established an industrially advantageous method for producing a long-chain .omega.-hydroxycarboxylic acid after finding that a long-chain .omega.-hydroxycarboxylic acid is produced by subjecting 2-(.omega.-alkoxycarbonyl alkanoyl)-4-butanolide to hydrolysis and decarboxylation and reducing the carbonyl groups in the resultant product into methylene groups.
The molecule of a typical long-chain dicarboxylate as used for the present invention contains two functional ester groups connected through a long methylene chain. Therefore, long-chain dicarboxylate is largely different from such compounds as oxalates that contain two functional ester grou
REFERENCES:
patent: 5023351 (1991-06-01), Yoshida et al.
Etoh Takeaki
Hata Go
Ito Nobuhiko
Katou Tetsuya
Dentz Bernard
Miller Austin R.
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