Hydrochloric Acid → Methyl 5,5-dimethyl-2-oxocyclohexane-1-carboxylate

Participants

Reaction Steps

To a suspension of hexane-washed NaH (0.72 g, 60%, 18 mmol) in tetrahydrofuran (30 mL) was added a solution of 4,4-dimethylcyclohexanone (2.0 g, 15.6 mmol) in tetrahydrofuran (20 mL). The suspension was stirred at room temperature for 30 minutes. Then dimethylcarbonate (6.31 mL, 75 mmol) was added dropwise by syringe. The mixture was heated to reflux for four hours. The mixture was acidified with 5% HCl and extracted with dichloromethane (100 mL×3) and washed with water, brine, and dried over Na2SO4. After concentration, the crude product was loaded on a column and eluted with 10% ethyl acetate in hexane to give title compound.

Provenance & Evidence