Potassium Hydroxide → 4-methyl-4-phenylcyclohexanone

Reaction equation

[CH:1]([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)=O.O.NN.[OH-].[K+]>C(O)CO>[CH3:1][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

Participants

Procedure

A mixture of 9.3 g. (0.038 mole) of 4-formyl-4-phenyl cyclohexanone, ethylene ketal (prepared in Example 30), 5 ml. of hydrazine hydrate and 6.4 g. of potassium hydroxide in 120 ml. of ethylene glycol is heated at reflux for about 1 hour. The solvent is then allowed to distill until the pot temperature comes to about 200°C. After about 5 hours the mixture is allowed to cool and then diluted with water and brine and evaporated to dryness. The residue is chromatographed on 750 ml. of Florisil (magnesium silicate) with elution by 1% ethyl acetate in Skellysolve B. The crystalline fractions are combined and recrystallized from a mixture of methanol and water to give 5.92 g. (67% yield) of 4-methyl-4-phenylcyclohexanone, ethylene ketal, having a melting point of 48° to 50°C.