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

Temperature

45 °C

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).

1. customat room temperature
2. customovernight
3. distillationThe solvent was distilled away under reduced pressure
4. additionto the residue was added 35% aqueous sodium hydroxide
5. stirringThe resultant mixture was stirred at 40-50° C. for 10 minutes
6. additionethyl acetate was added to the mixture
7. customto partition the mixture
8. extractionThe aqueous layer was extracted with ethyl acetate 4 times
9. dry with materialthe combined organic layer was dried over sodium sulfate anhydrate
10. distillationThe solvent was distilled away under reduced pressure

ORD record

ord-8be807fd4a5e48fcb394864f72c0a6dd

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07576135B2