Abstract:
2,6,10-TRIMETHYLDODECA-2,6,11-TRIEN-10-OL-1-AL (I) and its acetals and a process for the production of these important precursors of sinensal via the new acetals of 2,6-dimethyl-2,6undecadien-10-on-1-al (V). (I) is obtained from acetals of 2methyl-6-oxo-hept-2-en-1-al by vinylation or ethynylation followed by partial hydrogenation; reaction of the new allyl alcohols obtained with diketene or an acetoacetic ester to form the new acetals (V); vinylation or ethynylation followed by partial hydrogenation of the new acetals (V) and acid hydrolysis.
Abstract:
Production of alk-1-en-5-ones and alk-1-en-5-als having the general formula (I): in which R1, R2 and R3 each denotes a hydrogen atom or a hydrocarbon radical having from one to 40 carbon atoms which may be joined together in pairs to form five-membered to sevenmembered rings and which may contain oxygen atoms as heteroatoms and in which R4 denotes a hydrogen atom or a hydrocarbon radical having one to 40 carbon atoms which may also contain oxygen atoms as heteroatoms. Said compounds I being formed by reacting an allyl alcohol having the formula (II): at a temperature of from 50* to 350* C. with an acyl malonate having the formula (III): in which the radicals R5 and R6 denote identical or different alkyl groups having from 1 to 8 carbon atoms, and the resultant intermediate product having the general formula (IV): is hydrolyzed and decarboxylated.