Hydrochloric Acid → Methyl 4-methyldodecanoate

Participants

Reaction Conditions

Reaction Steps

An ether solution of the Grignard compound obtained from n-chlorooctane is added dropwise, under nitrogen, to a solution of ethyl levulate in ether, cooled to 0° C. The resulting lactone, 5-methyl-5-octyltetrahydrofuran-2-one (II), is converted with methanolic hydrochloric acid to methyl 4-chloro-4-methyldodecanoate (III), which, after eliminating hydrochloric acid by heating and then carrying out hydrogenation, gives racemic methyl 4-methyldodecanoate (IV), from which 4-methyldodecanoic acid (V) is obtained by hydrolysis. At the same time, the tosylate is prepared from 2-hexanol and, when reacted with sodium malonate in ethanolic solution, forms ethyl 2-carbethoxy-3-methylheptanoate (VI). This is converted to racemic 3-methylheptanoic acid (VII) by hydrolysis and thermal decarboxylation.

Provenance & Evidence