Process for the manufacture of gamma-acetoxytiglic aldehyde

Details Process for the manufacture of gamma-acetoxytiglic aldehyde Process for the manufacture of gamma-acetoxytiglic aldehyde

1994-09-30

1995-09-26

Lone, Werren B.

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

Organic compounds

Oxygen containing

568448, 568449, 568467, 568496, C07C 4540, C07C 4528, C07C 4527

Patent

active

054535476

ABSTRACT:
A novel process for the manufacture of .gamma.-acetoxytiglic aldehyde ("C.sub.5 -aldehyde"), which is known as an important starting material for the production of vitamin A acetate from a (.beta.-ionylidenethyl)triphenylphosphonium halide and C.sub.5 -aldehyde, comprises treating a pentenyn-3-ol of the formula HC.tbd.C--C(CH.sub.3)(OH)--CH.dbd.C(R).sub.2 (II), wherein both R's signify either hydrogen or methyl, with ozone, preferably in a lower alkanol R.sup.1 OH, wherein R.sup.1 signifies C.sub.1-4 -alkyl, to obtain an aldehyde 2-hydroxy-2-methyl-3-butynal of the formula HC.tbd.C--C(CH.sub.3)(OH)--CHO (III). The aldehyde III may be converted to the C.sub.5 -aldehyde by conventional means.

REFERENCES:
patent: 3639437 (1972-02-01), Fischer et al.
Geraghty and Morris, Papers, pp. 603-607 Aug. 1989.
Stevens, et al., Jo. of the Amer. Chem. Society, 108, 1039-1049 1986.
FR 2 383 908 Abstract for Document B1 1978.
FR 2 266 689 Abstract for Document B2 1975.

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