2-(N-chloroacetyl-2,6-dimethylphenylamino)cyclopentanol → HCID 12491483, compound

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Reaction Steps

A 4.5-ml (0.004-mol) sample of Jones Reagent (26.72 g chromium trioxide in 23 ml of concentrated sulfuric acid diluted with H2O to 100 ml) was added dropwise to a vigorously stirred solution of 4.4 g (0.016 mol) 2-(N-chloroacetyl-2,6-dimethylphenylamino)cyclopentanol in 100 ml acetone. The acetone solution was decanted from the solids, dried over magnesium sulfate, treated with silica and evaporated under reduced pressure to give 3.7 g of pale yellow oil. The oil was chromatographed on silica gel using mixtures of ethyl ether/hexane as eluant. 2-(N-chloroacetyl-2,6-dimethylphenylamino)cyclopentanone was eluted with 25% ethyl ether/hexane, as a white solid. This product melted at 79°-82° C. after recrystallization from hexane. This product is tabulated in Table I, as Compound No. 1-A.

Provenance & Evidence