N,N,N',N'-Tetramethylethylenediamine → Cyclohexanecarboxylic acid, 4-(hydroxymethyl)-, methyl ester

Participants

Reaction Conditions

Reaction Steps

Zinc borohydride solution (67 ml of a 0.35M solution, Ref. W. J. Gensler et al J Amer. Chem. Soc. 1960, 82, 6074) and tetramethylethylendiamine (TMEDA) were successively added to a stirred solution of 4-methoxycarbonylcyclohexylcarbonyl chloride (1.02 g) in THF (18 ml) at 0° C. The reaction mixture was stirred at 0° C. for 30 minutes. The organic phase was then washed with dilute hydrochloric acid and brine before drying over anhydrous magnesium sulphate and then evaporation in vacuo. Methyl 4-hydroxymethylcyclohexanecarboxylate was obtained as a semi-crystalline oil.

Provenance & Evidence