Formic Acid → (1R,2R)-1,2-Cycloheptanediol

Participants

Reaction Conditions

Reaction Steps

Cycloheptene (3.85 g) was added in small portions to 30% hydrogen peroxide (45 mL) and 88% formic acid (180 mL), and the thus-obtained mixture was stirred for 1 hour at 40-50° C., and then at room temperature overnight. The solvent was distilled away under reduced pressure, and to the residue was added 35% aqueous sodium hydroxide, to thereby make the mixture basic. The resultant mixture was stirred at 40-50° C. for 10 minutes, and ethyl acetate was added to the mixture to partition the mixture. The aqueous layer was extracted with ethyl acetate 4 times. The organic layers were combined, and the combined organic layer was dried over sodium sulfate anhydrate. The solvent was distilled away under reduced pressure, to thereby give the title compound (4.56 g).

Provenance & Evidence