Pinacolone → Methyl pivaloylacetate

Participants

Reaction Conditions

Reaction Steps

3,3-Dimethyl-2-butanone (10 g; 0.10 mol) was dissolved in DMSO (50 mL) and dimethyl carbonate (27 g; 0.30 mol; 3.0 equiv) was added. Sodium methoxide (10.8 g; 0.20 mol; 2.0 equiv) was added, resulting in a temperature rise to 30° C. The reaction mixture was heated to 40-50° C. for 4 h and then cooled to room temperature overnight. The reaction was quenched into a mixture of water (25 mL) and concentrated HCl (25 mL). Toluene (25 mL) was added and an additional 25 mL of water was added to dissolve salts. The layers were allowed to settle and the lower aqueous layer was removed and discarded. The organic layer was washed with water (25 mL), dried (Na2SO4), and filtered to afford 60 g of a toluene solution of 11. Analysis of this solution indicated 18.2 wt % of 11 to indicate a 69% yield.

Provenance & Evidence