Water → HCID 20379140, compound

Participants

Reaction Conditions

Reaction Steps

The 4-(3-methylpent-3-yl)cyclohexanol (350 g, 1.9 mol) prepared above was added slowly over a 3 hour period to a stirring solution of sodium dichromate (614 g, 2.06 mol), water (3.0 liters) and 98% sulfuric acid (526 g) while maintaining the batch temperature at 50°-55° C. Upon completion of the addition, the mixture was stirred an additional hour at 50° C. The reaction mixture was cooled and three liters of benzene was added. The layers were separated and the organic layer washed with one liter portions of water until a neutral pH was indicated. The solvent was removed on a rotary evaporator. Distillation of the residual oil under vacuum gave the desired 4-(3-methylpent-3-yl)cyclohexanone: 274 g, 79% theory; bp 105° C. (0.5 mm); mol wt 182 (ms); nmr, 0.75 (3H, s, methyl, 0.8 (6H, t, J=7, methyls), 1.15-2.0 (9H, m, CH, CH2), 2.15-2.5 (4H, m, Hα to carbonyl); ir, 2980, 2890, 1720, 1465, 1390, 1170 cm-1.

Provenance & Evidence