Cyclopropyl methyl ketone → 1,3-Dicyclopropylpropane-1,3-dione

Temperature

52.5 °C

Cyclopropyl methyl ketone (10.8 g; 0.2 mol) and MCPC (40 mL; 0.4 mol; 2 equiv) were dissolved in DMSO (100 mL) and sodium methoxide (21.6 g; 0.4 mol; 2 equiv) was added. The resulting mixture was heated to 50-55° C. for 4-6 h and then cooled overnight to room temperature, The reaction mixture was quenched into 100 mL of 18% HCl. Water (50 mL) and toluene (50 mL) were added. The layers were thoroughly mixed and allowed to settle. The lower aqueous layer was removed and extracted with a second portion of toluene (25 mL). The combined toluene solution was washed with water (50 mL), dried with sodium sulfate, and concentrated. The residue was vacuum distilled to afford two fractions which were 92 and 99.5% pure 10, respectively.

1. temperaturecooled overnight to room temperature
2. customThe reaction mixture was quenched into 100 mL of 18% HCl
3. additionWater (50 mL) and toluene (50 mL) were added
4. additionThe layers were thoroughly mixed
5. customThe lower aqueous layer was removed
6. extractionextracted with a second portion of toluene (25 mL)
7. washThe combined toluene solution was washed with water (50 mL)
8. dry with materialdried with sodium sulfate
9. concentrationconcentrated
10. distillationdistilled
11. customto afford two fractions which

ORD record

ord-59c071db9a0a499a91afdd8455b4b9b2

Source dataset

uspto-grants-2000_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06143935