Hydrochloric Acid → 2,3-Dimethyl-4-Phenyl-2,3-Butanediol

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Reaction Steps

A solution of 41 g. of 3-hydroxy-3-methyl-2-butanone in 300 ml. of dry tetrahydrofuran was treated at -10° under nitrogen with 500 ml. of 2M benzyl magnesium chloride and stirred at 25° C. for 20 hours. An aqueous ammonium chloride solution was added at 0° and the mixture was acidified at 0° with concentrated hydrochloric acid and extracted with ethyl acetate. The extract was evaporated and the residue chromatographed on silica gel. Elution with 20% ethyl acetate in hexane followed by recrystallization from the same solvent afforded 38 g. of the title product, m.p. 72°-74°, λmaxKBr 2.95, 3.35, 6.2, 6.63, 6.82, 7.23, 7.45, 7.65, 8.32, 8.70, 9.13, 10.58, 11.0, 11.40, 12.30, 12.97 and 14.06 μ.

Provenance & Evidence