2-ISOPROPYL-5-METHYL-2-HEXENAL, 2-ISOP-ROPYL-5-METHYLHEXANAL,3-HYDROXY-2-ISOPROPYL-5-METHYLHEXANAL, AND DERIVATIVES THEREOF AS TOBACCO FLAVORANTS

摘要

The base-catalyzed self-condensation of isovaleraldehyde yields a mixture of threo- and erythro-2-isopropyl-5-methyl-3-hydroxyhexanal. The reaction conditions can be so chosen as to favor predominance of one isomer over the other. Upon vacuum distillation of the mixture, one of the isomers preferentially dehydrates yielding 2-isopropyl-5-methyl-2-hexenal as a distillate and unchanged 3-hydroxy-2-isopropyl-5-methylhexanal as the residue. These aldehydes are the parent members of a class of compounds composed of 2-isopropyl-5-methylhexanal, 3-hydroxy-2-isopropyl-5-methylhexanal, 2-isopropyl-5-methyl-2-hexenal, and the alcohol and carboxylic acid derivatives of these aldehydes, the ester and ether derivatives of the alcohols and acids, as well as certain other alcohol and ketone derivatives. These compounds are useful as tobacco additives to modify the taste of the tobacco, and/or as intermediates for the preparation of tobacco additives.