Ethyl bromoacetate → 2,7-Dimethyloctanedioic acid

Participants

Reaction Steps

As processes for synthesizing 3,8- or 3,7-dimethyldecanedioic acid, the following (7) through (9) are known: (7) a process for synthesizing 3,8-dimethyldecanedioic acid, from 2,7-octanedione comprising the five steps of Reformatsky reaction of ethyl bromoacetate, bromination of hydroxyl group, dehydrobromination, hydrogenation of double bond and hydrolysis of ester (see Ann., 580, 125-131 (1953)); (8) a process for synthesizing 3,8-dimethyldecanedioic acid, comprising seven steps starting from malonic condensation of diethyl methylmalonate and 1,4-dibromobutane, followed by hydrolysis and decarboxylation to obtain 2,7-dimethyloctanedioic acid as an intermediate and the subsequent conversion of this intermediate to acid chloride, which is then converted via diazoketone into the intended dicarboxylic acid (see Ann., 598, 1-24 (1956)); (9) a process to obtain 3,7-dimethyldecanedioic acid by hydrogenation of essential oil of Geranium macrorhizum, and subsequent ozonolysis and degradation with perchloric acid (see Chem.listy, 52, 1174-1179 (1958)).

Provenance & Evidence