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

Temperature

45 °C

Cycloheptene (3.85 g) was added portionwise to 30% aqueous hydrogen peroxide (45 ml) and 88% formic acid (180 ml), and the mixture was stirred at 40 to 50° C. for 1 hour and then at room temperature for a night. The solvent was distilled off under reduced pressure, and a 35% aqueous solution of sodium hydroxide was added to the residue to alkalify it. After this residue was stirred at 40 to 50° C. for 10 minutes, ethyl acetate was added to conduct liquid separation. The resultant water layer was extracted 4 times with ethyl acetate. The resultant organic layers were collected and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain the title compound (4.56 g) as a colorless oil.

1. waitat room temperature for a night
2. distillationThe solvent was distilled off under reduced pressure
3. additiona 35% aqueous solution of sodium hydroxide was added to the residue
4. stirringAfter this residue was stirred at 40 to 50° C. for 10 minutes
5. additionethyl acetate was added
6. customliquid separation
7. extractionThe resultant water layer was extracted 4 times with ethyl acetate
8. customThe resultant organic layers were collected
9. dry with materialdried over anhydrous sodium sulfate
10. distillationthe solvent was distilled off under reduced pressure

ORD record

ord-43a846cd745a493da99b80bb9358b456

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07935824B2