Ethylene Glycol → HCID 54050571, compound

Participants

Reaction Steps

A stirred solution of ethyl (4-keto-2-phenyl cyclohex-2-enyl)acetate (12.91 g.), p-toluene sulphonic acid monohydrate (0.95 g.) and ethylene glycol (2.93 ml.) in benzene (258 ml.) was heated under reflux using a Dean and Stark water separator for 2.5 hours. A further aliquot of ethylene glycol (0.7 ml.) was then added and the mixture heated under reflux for a further 3 hours. The reaction mixture was then cooled and the benzene evaporated. The residual mixture was dissolved in ether (500 ml.). The solution was extracted with saturated sodium bicarbonate solution (2×100 ml.). The combined extracts were washed with water (2×100 ml.), dried (MgSO4) and evaporated under reduced pressure. The crude product was purified by flash chromatography on silica, eluting with ether/hexane (3:1 v/v), to give the ethylene ketal of ethyl (4-keto-2-phenylcyclohex-1-enyl)acetate (9.35 g.) NMR (90 MHz): 1.20 (3H,t), 1.88 (2H,t). 2.38 (2H,t), 2.9 (2H,s), 4.0 (4H,s), 4.1 (2H,q) and 7.1-7.4 (5H,)ppm.

Provenance & Evidence