Hydrochloric Acid → 1-Cyclohexene-1-carboxylic acid, ethyl ester

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Reaction Steps

Methyl 2-cyclohexene-1-carboxylate (5.6 g; 40 m. moles) was added to a solution of sodium (1.1 g; 47.8 m. moles) in ethanol (35 ml) and the mixture was allowed to stand at room temperature for a period of 11/2 hours. The mixture was poured into dilute hydrochloric acid extracted with ether (4×25 ml) and the combined extracts washed with dilute aqueous sodium carbonate. The dried (MgSO4) extract was evaporated and the residue distilled to give ethyl 1-cyclohexene-1-carboxylate (5.5 g; yield 90%), b.p. 92° C./15 mm (N.M.R.: 6.7-7.0 (m,1,CH=C), 3.9-4.25 (q,2,CH2CH3), 1.95-2.42 (m,4,allylic CH2), 1.13-1.42 (t,3,CH2CH3) 1.45-1.92 (m,4,CH2 --CH2)).

Provenance & Evidence