Dimethyl Carbonate → Methyl 4,4-dimethyl-2-oxocyclohexane-1-carboxylate

Reaction equation

[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH2:3]1.[H-].[Na+].[C:12](=O)([O:15]C)[O:13][CH3:14]>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][CH:5]([C:12]([O:13][CH3:14])=[O:15])[C:4](=[O:8])[CH2:3]1

Participants

Procedure

A solution of 3,3-dimethylcyclohexanone (0.5 g, 3.97 mmol, 1 equiv) and sodium hydride in toluene was stirred at rt for half an hour. To the mixture was added dimethyl carbonate and heated at reflux for 5 h. After the reaction was cooled to rt, the reaction mixture was quenched with water and extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine and dried over anhydrous sodium sulfate, then concentrated under reduced pressure to give the crude product, which was directly used for the next step.