An improved method of preparation of halopropargyl alcohol is described. Hydration of halopropargyl alcohol followed by hydrolysis gave dihydroxyacetone which was identified as its dibenzoate. 2-Butyne-1,4-diol was converted into acetoxymethyl vinyl ketone. 1,4-Diacetoxy-3-bromobutan-2-one obtained by the addition of acetyl hypobromite to the vinyl ketone was treated with silver acetate to yield tri-O-acetyl-Dl-erythrulose. Hydrolysis of the triacetate afforded Dl-erythrulose which was identified as phenylhydrazone.
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Ando et al. (1972) studied this question.
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