Preparation of 5-hydroxy-4-methyl-2(5H)-furanone

Details Preparation of 5-hydroxy-4-methyl-2(5H)-furanone Preparation of 5-hydroxy-4-methyl-2(5H)-furanone

1996-03-22

1997-08-05

Dentz, Bernard

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D30760

Patent

active

056544448

ABSTRACT:
5-Hydroxy-4-methyl-2(5H)-furanone is prepared by cyclization of alkyl .beta.-formylcrotonates by heating with dilute aqueous hydrochloric acid or, advantageously, in the presence of dilute aqueous hydrochloric acid and catalytic amounts of methanol as solubilizer, subsequent workup of the reaction mixture by distillation and, where appropriate, isomerization of the 5-methoxy- or 5-ethoxy-4-methyl-2(5H)-furanone, which is formed as byproduct, by heating with dilute hydrochloric acid.

REFERENCES:
Geoffrey K. Cooper, et al. "Convenient Synthesis of the 2-Methyl-4-Hydroxybut-2-Enolide Moiety of Strigol", Journal of Organic Chemistry, vol. 44, No. 19, 1979, pp. 3414-3416.
J.J. Bourguignon, et al. "Lactone Chemistry. Synthesis of .beta.-Substituted, .gamma.-Functionalized Butanolides and Butenolides and Succinaldehydic Acids from Glyoxylic Acid", Journal of Organic Chemistry, vol. 46, 1981, pp. 4889-4894.
Wiley et al., J.A.C.S., vol. 78, pp. 808-810 (1956).
A. W. Johnson et al. "The Preparation of Synthetic Analogues of Strigol", Journal of the Chemical Society, Perkin Transactions 1, No. 6, (1981), pp. 1734-1743 and 1735.
Database WPI, Week 9435, Derwent Publications Ltd., London, GB; AN 94-283338 (1994).

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