Propylene Glycol → 2,4-Dimethyl-2-(3-methyl-2-chloroacetamidophenyl) dioxolane

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Reaction Steps

N-chloroacetyl-2-methyl-6-acetylaniline (from Example 1), 4.51 g, 1,2-propanediol, 3.7 ml, and a dash of toluene sulfonic acid were combined in 50 ml toluene and refluxed. The distilled water by-product was collected in a Dean-Stark trap. After water ceased to distil, methylene chloride was added and the mixture was extracted successively with bicarbonate solution and water, then dried (MgSO4) and evaporated to yield 3.3 g brown oil. The oil was purified on a silica gel column (Hexane:ethyl acetate eluant) to yield the title product (Compound No. 2 in Table A).

Provenance & Evidence