Sodium Hydroxide → trans-1,2-Dimethylcyclohexene-4,5-dicarboxylic acid

Participants

Reaction Steps

Trans-dimethyl 1,2-dimethylcyclohex-1-ene-4,5-dicarboxylate (4.52 g, 0.02 mol) was refluxed with NaOH (4.0 g, 0.1 mol) in methanol (40 ml) for 4 hr. The solution was allowed to cool and partitioned between aqueous NaOH (2M, 50 ml) and ether (60 ml). The aqueous layer was then acidified (1M HCl) and extracted with ethyl acetate (3×50 ml). The solvent was removed in vacuo to give the title compound in 77% yield. N.m.r: δH (90 MHz CD3Cl3) 2.58 (m,2H), 2.08 (m,4H), 1.70 ppm (s,6H)

Provenance & Evidence