Ethylene Glycol → (1-Allylcyclohexyl)benzene

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-allyl-2-phenylcyclohexanone (1.97 g, 9.19 mmol) in ethylene glycol (8 mL, 143 mmol) were added hydrazine (0.8 mL, 25 5 mmol) and potassium hydroxide (1.547 g, 27 6 mmol), and the mixture was stirred at 100° C. for 1 hr and refluxed in a 180° C. oil bath for 2.5 hrs. TLC showed that the hydrazone formation nearly complete. Then the excess hydrazine and water were distilled out in a 200° C. oil bath, and it was continued to heat at the same temperature for 4 hrs. After cooling to room temperature, the mixture was added to ether and washed with water and brine. The combined aqueous layers were back-extracted with ether (2×), combined, dried over Na2SO4, and evaporated to give an oily residue. It was purified by Combiflash (80 g silica gel) eluting with hexane followed by 5:95 EtOAc-hexane to give product (825 mg).

Provenance & Evidence