Process for the preparation of ethynylbenzaldehydes

Details Process for the preparation of ethynylbenzaldehydes Process for the preparation of ethynylbenzaldehydes

1988-05-09

1989-07-18

Gray, Bruce

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

Organic compounds

Oxygen containing

568424, 568583, 568592, C07C 47548

Patent

active

048495468

ABSTRACT:
A multi-step process for the preparation of ethynylbenzaldehydes from bromo- or iodobenzaldehydes is disclosed. The arylhalogen is replaced with a protected ethynyl compound which is subsequently cleaved by base to form the arylacetylene. The aldehydic functionlity is preserved by formation of a corresponding Schiff's base or acetal, and its subsequent regeneration by treatment with aqueous acid.

REFERENCES:
patent: 4178430 (1979-12-01), Billow
patent: 4283557 (1981-08-01), Walton
patent: 4336362 (1982-06-01), Walton
Ojima et al, Chemical Abstracts, vol. 77, no. 126305m (1972).
K. S. Y. Lau et al., J. Polymer Sci., Polymer chem. Ed. 21, 3009 (1983).
W. B. Austin et al., J. org. Chem. 46, 2280-86, (1981).
E. Goldberg et al., JACS, vol. 77, 359-361 (1955).
J. Ojima et al., CA vol. 77, 126305m (1972).
S. J. Havens et al., J. Org. Chem 50, 1763-65, (1985).

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