Acetone → HCID 21469874, compound

Participants

Reaction Steps

To a 250 mL round bottom flask containing 11.4 grams (36.3 mmole) of methyl ester 8 was added 70 mL of acetone and the mixture sonicated until solution was complete. To the solution was then added 15 mL of concentrated HCl, 20 mL of H2O and the resulting solution refluxed for 6 hours. At the end of 6 hours the volatile components of the reaction mixture were removed under reduced pressure to give an oil/water mixture which was then dissolved in 100 mL of CH2Cl2. The organic/aqueous mixture was then extracted with 150 mL of saturated NaHCO3. The aqueous layer was then removed and acidified with concentrated hydrochloric acid to a pH equal to 1. The aqueous mixture was then quickly extracted with 100 mL of CH2Cl2. The organic layer was then dried over MgSO4, filtered and the volatile components removed under reduced pressure to give an oil which crystallized to give 6.0 grams (64% yield) of 9 as a white solid.

Provenance & Evidence