Hydrochloric Acid → 4-(4-Isopropylphenoxy)-1-cyclohexanone

Participants

Reaction Steps

In 40 ml of anhydrous tetrahydrofuran were dissolved 4.00 g of 4-isopropylphenol, 5.10 g of 1,4-dioxaspiro[4.5]decan-8-ol and 8.47 g of triphenylphosphine. Then, 14.1 g of 40% solution of diethyl azodicarboxylate in toluene was dropwise added at 0-5° C., and the resulting mixture was stirred at ambient temperature for 24 hours. The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduce pressure. Ethyl ether was added to the residue, the deposited insoluble matter was filtered off, and the filtrate was concentrated under reduced pressure. The residue thus obtained was mixed with 60 ml of anhydrous tetrahydrofuran and 40 ml of 6 mol/L hydrochloric acid and stirred at ambient temperature for 24 hours. The reaction mixture was poured in a mixture of water and ethyl acetate, and the organic layer was separated. The organic layer was washed successively with water and saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Purification of the residue by column chromatography [eluents: toluene:ethyl acetate=20:1, followed by hexane:ethyl acetate=20:1] gave 2.40 g of 4-(4-isopropylphenoxy)-1-cyclohexanone as a colorless oily product.

Provenance & Evidence