Method of preparation of 8-hydroxyoctanoic acid

Details Method of preparation of 8-hydroxyoctanoic acid Method of preparation of 8-hydroxyoctanoic acid

1991-07-22

1993-09-28

Dees, Jose G.

Organic compounds -- part of the class 532-570 series

Organic compounds

Fatty compounds having an acid moiety which contains the...

C07C 5700

Patent

active

052487989

DESCRIPTION:

BRIEF SUMMARY
DESCRIPTION

The present invention refers to a novel and advantageous method of preparation of 8-hydroxyoctanoic acid with formula I and its salts


DESCRIPTION OF THE PRESENT STATE OF THE ART

.omega.-Hydroxycarboxylic acids with 2-6 carbon atoms together with their salts, esters and lactones are established technical products; .omega.-hydroxycarboxylic acids with 9-11 carbon atoms are obtained, in part, semisynthetically from natural products (oleic acid, castor oil etc.), higher members are prepared, for example, by the reaction of cyclic enamines with .omega.-acyloxycarboxylic acid chlorides (cf. G. Schill, Chem. Ber. 99, 2689 (1966).
Some methods are also known for the preparation of 7-hydroxyheptanoic acid and 8-hydroxyoctanoic acid. Thus, 7-hydroxyheptanoic acid is accessible from 7-chloroheptanoic acid (A. N. Nesmeyanov, L. I. Zakharkin, Izvest. Akad. Nauk. U.S.S.R., Otdel. Khim. Nauk. 1955, 224-32; Bull. Acad. Sci. U.S.S.R., Div. Chem. Sci. 1955, 199-205 (C.A. 1956, 4849)), furanacrylic acid (E. V. Hort, U.S. Pat. No. 2,955,133 (1960)), alkoxytetrahydropyranes (A. E. Montagna, D. G. Kubler, J. J. Brezinski, U.S. Pat. No. 2,998,466 (1961)) or from cycloheptanone by Baeyer-Villiger oxidation (Neth. Appl. 6511967 (1966), C.A. 65, 3995h (1966); R. Robinson, L. H. Smith, J. Chem. Soc. 1937, 371-4).
8-Hydroxyoctanoic acid which is a component of gelee royale (cf. N. Weaver, N. S. Johnston, R. Benjamin, J. H. Law, Lipids 3, 535-8 (1968), C.A. 70, 55231b (1969)) and its esters can, apart from some low-yield routes (from octanoic acid, cf. M. Kusunose, E. Kusunose, H. J. Coon, J. Biol. Chem. 239, 1374-80 (1964); from the nitrile of oleic acid, cf. J. Pasero, L. Comeau, M. Naudet, Bull. Soc. Chim. France 1963, 1794-8; from octandioic acid by reduction with hydrogen, cf. A. N. Bashkirov, L. A. Morozov, A. I. Prudnikov, Neftekhimiya 16, 230-4 (1976), C.A. 85, 77548x (1976); via the methyl ester of 8-acetoxy-6-oxooctanoic acid or its ethylenethioketal, cf. S. Yurugi et al., Ann. Rep. Takeda Res. Lab. 27, 34-42, (1968), C.A. 70, 77899c (1969), H. Hagiwara et al., Japan Patent 19323 (65), C.A. 1965, 16218c; from the lactam of N-nitroso-8-aminooctanoic acid, cf. R. Huisgen, J. Reinertshofer, Justus Liebigs Ann. Chem. 575, 174-97 (1952), C.A. 47, 3812h; via .beta.-2-thenoylpropionic acid, cf. E. Schwenk et al., Org. Syntheses 27, 68-71, (1947)), be prepared by the reduction of octandioic monoester acid chloride with sodium borohydride (H. J. Bestmann, R. Kunstmann, H. Schulz, Justus Liebigs Ann. Chem. 699, 33-9 (1966), C.A. 66, 54981b (1967)), by the reduction of the potassium salt of octandioic acid monomethyl ester with sodium in ethanol (P. Chuit and J. Hausser, Helv. Chim. Acta 12, 463-92, (1929), C.A. 23, 3663 (1929)), via the oxidation of 6-chlorohexanol to 6-chlorohexanal, condensation of the aldehyde with malonic acid, decarboxylation to 8-chloro-2-octenoic acid, conversion to 8-hydroxy-2-octenoic acid and hydrogenation of the double bond (R. Achard and J. Morel, Fr. 1355775, C.A. 61, 4222h (1964)) or by Baeyer-Villiger oxidation of cyclooctanone (Neth. Appl. 6511967, C.A. 65, 3995h (1966); E. E. Smissman, J. F. Muren, N. A. Dahle, J. Org. Chem. 29, 3517-20 (1964), C.A. 62, 2703a (1965); S. L. Friess and P. E. Frankenburg, J. Am. Chem. Soc. 74, 2679 (1952)).
A further synthetic route to 8-hydroxyoctanoic acid and its salts starting from 1,6-dichlorohexane and dialkyl malonates has been described by H. Lautenschlager et al. (DE-OS 34 01 913).
The 8-hydroxyoctanoic acids and their salts are valuable intermediates for the synthesis of pharmacologically active 2-imidazolyloxyalkane carboxylic acids and in particular octimibate (H. Lautenschlager et al., DE-OS 32 28 271).
The purpose of this invention is to provide a preparation method for 8-hydroxyoctanoic acid and/or its salts that requires less expense than present methods and which is characterized by a better overall yield.
This purpose is achieved by:
Method for the preparation of 8-hydroxyoctanoic acid and its salts according to formula I reacting alcoho

REFERENCES:
patent: 3404166 (1968-10-01), Achard et al.
patent: 3708534 (1973-01-01), Ishimoto et al.
Chemical Abstracts, vol. 104, #11, p. 620, 1986.

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