Process for the oxidation of organic halides to organic aldehyde

Details Process for the oxidation of organic halides to organic aldehyde Process for the oxidation of organic halides to organic aldehyde

1984-12-20

1986-04-01

Lone, Werren B.

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

Organic compounds

Oxygen containing

C07C 4527

Patent

active

045799776

ABSTRACT:
Process for the conversion of organic halides to organic aldehydes is provided wherein a mixture consisting essentially of organic halide and dimethyl sulfoxide is first heated to a temperature of about 40.degree.-100.degree. C. for a time in the range of about 0.1-12 hours, then sodium bicarbonate is added and thereafter the resulting mixture further heated to a temperature in the range of about 90.degree.-180.degree. C. for an additional time in the range of about 0.1-12 hours. In a specific embodiment of the invention, a cosolvent selected from the group consisting of dimethylphthalate, triglyme and caprolactone is added along with the sodium bicarbonate prior to the second heating step. In another specific embodiment of the invention, the second heating step is carried out under reduced pressure conditions. The formation of alcohol by-product is greatly reduced in the practice of the present invention. Thus higher yields and easier recovery of the desired aldehyde product are achieved.

REFERENCES:
patent: 2888488 (1959-05-01), Nace
patent: 4174352 (1979-11-01), Fisher et al.
patent: 4175204 (1979-11-01), Babler
patent: 4335263 (1982-06-01), Minai
Nace, "J. Organic Chem.", vol. 24, p. 1792.
Kornblum et al., "J. Amer. Chem. Soc.", vol. 79, p. 6562 (1957).
Ganem et al., "Tetrahedron Letters", No. 11, pp. 917-920 (1974).

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