Pyridine → (4-Oxo-1-phenylcyclohexyl)methyl acetate

Reaction equation

[OH:1][CH2:2][C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.N1C=CC=CC=1.[C:22](OC(=O)C)(=[O:24])[CH3:23]>O>[C:22]([O:1][CH2:2][C:3]1([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:4][CH2:5][C:6](=[O:9])[CH2:7][CH2:8]1)(=[O:24])[CH3:23]

Participants

Procedure

6.6 g. of 4-hydroxymethyl-4-phenylcyclohexanone is dissolved in 40 ml. of pyridine and 20 ml. acetic anhydride. After about 20 hours of standing at room temperature, the mixture is poured into ice and water. The gum that precipitates is extracted with ether. The organic layer is washed successively with water, 2.5 N hydrochloric acid, water, sodium bicarbonate solution, and brine, and then evaporated to dryness. The solid residue is recrystallized from Skellysolve B to give 6.74 g. (35.8% yield) of 4-acetoxymethyl-4-phenylcyclohexanone, having a melting point of 74° to 79°C.