Ethylene Glycol → 2-Methyl-2-[2-(4-methylbenzene-1-sulfonyl)ethyl]-1,3-dioxolane

Participants

Reaction Steps

A stirred mixture of 4-toluenesulphinic acid (23.7 g, 0.15 mole) and ethylene glycol (30 ml) was treated over 10 minutes with methyl vinyl ketone (6.3 ml, 0.075 mole). The reaction was slightly exothermic and gave a clear solution. This was stirred at room temperature for 6h, during which time a white precipitate formed. The mixture was poured into ice/water (600 ml) containing conc. ammonia solution (20 ml) and on vigorous stirring a white solid crystallised. This was filtered off, washed with water, dried and recrystallised from propan-2-ol/60-80 petrol to give the title compound (D25) as a white solid (15.2 g, 75%) m.p. 122°-123° C.

Provenance & Evidence