Hydrochloric Acid → 1-(4-Benzyloxy-phenyl)-2-ethyl-4-hydroxymethyl-3-methyl-cyclohexanol

Participants

Reaction Conditions

Reaction Steps

1-Benzyloxy4-iodo-benzene (5.70 g, 18.37 mmol) was dissolved in anhydrous THF (36 mL) at −10° C. Isopropyl magnesium chloride (1.0 M, 18.37 mL) was added and the mixture was stirred for 3 h. A solution of 2-ethyl-3-methyl-4-trimethylsilanyloxymethyl-cyclohexanone (12.0 g in 50 mL THF) was added slowly over 30 min by syringe pump. The reaction mixture was stirred for 30 min at 25° C. and then refluxed for 30 min. The reaction mixture was then cooled to 25° C., HCl (1.0 N, 80 mL) was added slowly, followed by addition of ethyl acetate (100 mL). The organic layer was washed with H2O (100 mL), dried over MgSO4 and purified on SiO2 (10˜15% ethyl acetate/hexane) to yield 1-(4-benzyloxy-phenyl)-2-ethyl-4-hydroxymethyl-3-methyl-cyclohexanol.

Provenance & Evidence