1-chloro-1-methylcyclohexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 36.5 g of 2-methyl-2-chlorocyclohexane are dissolved in 70 ml ethanol. To this solution is added a mixture of 82 g benzylmercaptan 26.4 g of sodium hydroxide and 330 ml ethanol and the whole is heated to reflux. A pink colour appears after 15 minutes and the mixture is then allowed to cool to room temperature and the solvent is distilled off. The oily residue is taken up in 400 ml water and the resulting suspension is extracted with methylene chloride. The organic phases are united, washed with water until neutral, dried over sodium sulphate and the solvent is evaporated off. The residue is purified by fractional distillation. 120 g of 2-methyl-2-benzylthiocyclohexanone are recovered, boiling at 142°-144° (yield=78%). To this solution is added the whole is heated to reflux the solvent is distilled off the resulting suspension is extracted with methylene chloride washed with water until neutral, dried over sodium sulphate the solvent is evaporated off The residue is purified by fractional distillation 120 g of 2-methyl-2-benzylthiocyclohexanone are recovered