Pinacolone → Methyl pivaloylacetate

Temperature

45 °C

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.

1. customresulting in a temperature rise to 30° C
2. temperaturecooled to room temperature overnight
3. customThe reaction was quenched into a mixture of water (25 mL) and concentrated HCl (25 mL)
4. additionToluene (25 mL) was added
5. additionan additional 25 mL of water was added
6. dissolutionto dissolve salts
7. customthe lower aqueous layer was removed
8. washThe organic layer was washed with water (25 mL)
9. dry with materialdried (Na2SO4)
10. filtrationfiltered

ORD record

ord-99371f4ff6964c5b9ddc41a0fe890966

Source dataset

uspto-grants-2000_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06143935