Ammonia → 2-[2-(4-Methylbenzene-1-sulfonyl)ethyl]-1,3-dioxolane

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Reaction Steps

A mixture of sodium 4-toluenesulphinate monohydrate (37.2 g, 0 19 mole) and 2-(2-bromoethyl)-1,3-dioxolane (20 ml, 0.17 mole) in dry DMF (100 ml) was stirred at room temperature for 64 h, resulting in a homogenous solution. This was poured into ice/water (1 liter) containing conc. ammonia solution (100 ml) and stirred vigorously until a white precipitate formed. The solid was filtered off, washed with water, dried and recrystallised from propan-2-ol/ether to give the title compound (D24) as a white solid (28.7 g, 66%) m.p. 78-80° C.. 1H-NMR (CDCl3) δ:

Provenance & Evidence