Hydrogen Peroxide → HCID 14010391, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 15.0 g of 3-methallyl-4-pivaloyloxybenzophenone in 30 ml of THF was treated with 100 ml of 0.5M solution of 9-BBN in THF at 0° C. The mixture was stirred at 25° C. for 3 h and at 50° C. for 1 h. To the cooled reaction mixture were added 30 ml of ethanol, 9.5 ml of 6N sodium hydroxide, and 18 ml of 30% hydrogen peroxide. After stirring at 25° C. for 2 h, the oxidation mixture was treated with solid potassium carbonate followed by a small amount of water. The organic layer was separated and dried over MgSO4. The crude product (22 g) was chromatographed on a silica gel column using toluene-ethyl acetate. 8.0 g of product was obtained as an oil. Calcd. for C22H26O4 : C, 74.55; H, 7.39. Found: C, 74.30; H, 7.35.

Provenance & Evidence