Salicylic Acid → HCID 54122933, compound

Participants

Reaction Steps

To a solution of the barbituric acid derivative prepared in the preceding experiment (100 mg, 0.42 mmol) in 1.0 mL dichloromethane was added 6 mg (42 umol) salicylic acid and 9 mg (84 umol) selenium dioxide. The suspension was placed in a water bath, and 0.29 mL (3.8M, 1.09 mmol) of a anhydrous solution of tert-butyl hydroperoxide in benzene was added. The suspension was then vigorously stirred for 12 hours at ambient temperature. The reaction mixture was concentrated, and chromatographed directly on a silica gel column, eluting with 40%, 50%, 60%, and 70% ethyl acetate/hexane. In addition to some starting material as well as other products, 21 mg of a colorless oil was isolated.

Provenance & Evidence