1-Phenylethanol → Acetophenone

There were weighed out 1-phenylethanol (122 mg, 1.00 mmol) and 4-benzoyloxy-2,2,6,6-tetramethylpiperidine-N-oxyl compound (3.0 mg, 0.01 mmol). Then, 2 ml of acetone was added to obtain a uniform solution. Added thereto was 500 mg of silica gel (product of Merck, grade 9385) and the mixture was vigorously agitated for 5 minutes. The acetone used was distilled off under reduced pressure. Added thereto was 7% aqueous solution of sodium bicarbonate (5 ml) containing 20 wt % of sodium bromide. Then, the mixture was thoroughly stirred. Two platinum electrodes (1.5×1.0 cm) were applied to the mixture which was then subjected to electrolytic oxidation reaction for 2 hours while being vigorously stirred at room temperature and maintaining the current at 30 mA (quantity of electricity being 2.2 F/mol). After completion of reaction, silica gel was filtered off from the reaction mixture, extraction was effected with 5 ml of acetone and acetone was distilled off. The obtained residue was passed through silica gel column to adsorb it on the column, and elution was performed with a solvent mixture of ethyl acetate/hexane=7/1, giving 116 mg of acetophenone in a yield of 96%.

1. customto obtain a uniform solution
2. additionAdded
3. distillationThe acetone used was distilled off under reduced pressure
4. additionAdded
5. additioncontaining 20 wt % of sodium bromide
6. stirringThen, the mixture was thoroughly stirred
7. customwas then subjected to electrolytic oxidation reaction for 2 hours
8. stirringwhile being vigorously stirred at room temperature
9. temperaturemaintaining the current at 30 mA (quantity of electricity being 2.2 F/mol)
10. customAfter completion of reaction, silica gel
11. filtrationwas filtered off from the reaction mixture, extraction
12. distillationwas distilled off
13. washon the column, and elution
14. additionwas performed with a solvent mixture of ethyl acetate/hexane=7/1

ORD record

ord-f5b727f058fb4e4584e0c9f50ff762b3

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07183421B2