Process of preparing .alpha.-formyl sulfides and 2-hydrocarbylth

Details Process of preparing .alpha.-formyl sulfides and 2-hydrocarbylth Process of preparing .alpha.-formyl sulfides and 2-hydrocarbylth

1974-10-24

1976-01-06

Schwartz, Gerald A.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260465D, 260465E, 260465F, 260465G, 260465H, 260470, 260476, 260479S, 260481R, 260503, 260505R, 260505C, 260507R, 260508, 260509, 260511, 260513R, 260513N, 260514G, 260514H, 260514J, 260516, 260534S, 260563R, 26066A, 260584A, 260598, 260599, 260601H, 260946, C07C 4700

Patent

active

039313310

ABSTRACT:
An .alpha.-formyl sulfide is prepared by a process which comprises reacting in an aqueous medium an .alpha.-haloaldehyde of the formula ##EQU1## wherein R' and R" independently are hydrogen, hydrocarbon radicals of 1 to 18 carbon atoms selected from the group consisting of alkyl, cycloalkyl, alkenyl, cycloalkenyl and aryl, or substituted hydrocarbon radicals of the above group, and X is a halogen selected from the group consisting of chlorine, bromine, and iodine, with a thiol salt of the formula R"'SM, wherein R"' is a hydrocarbon radical of 1 to 18 carbon atoms selected from the group consisting of alkyl, cycloalkyl, alkenyl, cycloalkenyl and aryl or a substituted hydrocarbon radical of the above group; and M is an alkali or alkaline earth metal, thereby forming an .alpha.-formyl sulfide of the formula ##EQU2## Also, 2-hydrocarbylthioaldoximes are prepared by oximating the above .alpha.-sulfides by reaction with a source of hydroxylamine. Additionally, 2-hydrocarbylthioaldoximes are prepared by a process which comprises halogenating an aldehyde having the formula ##EQU3## wherein R' and R" are defined as above, to form an .alpha.-haloaldehyde of the formula ##EQU4## wherein X is defined as above, reacting in an aqueous medium the .alpha.-haloaldehyde with a thiol salt of the formula R"'SM, wherein R"' and M are defined as above, to form an .alpha.-formyl sulfide of the formula ##EQU5## and oximating the .alpha.-formyl sulfide to form a 2-hydrocarbylthioaldoxime of the formula ##EQU6##

REFERENCES:
wagner et al., "Synthetic Organic Chemistry" pp. 100-101 (1965).

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