Hydrochloric Acid → 1-Phenylhexan-3-one

Participants

Reaction Conditions

Reaction Steps

6.8 g of sodium hydroxide prills (170 mmol) in 100 ml of a nonane fraction (b.p.: 148-153° C.) were initially introduced at room temperature into a three-necked flask having a reflux condenser, internal thermometer and stirrer. After 20 g of 3-hydroxy-3-(2′-phenylethyl)hexanoic acid (85 mmol), prepared according to K. S. Fors, J. R. Gage, R. F. Heier, R. C. Kelly, W. R. Perrault and N. Wicnienski, J. ORG. CHEM. 63, 7348 (1998), had been added, the mixture was heated to 155° C., a clear solution initially forming. The mixture was stirred for 2 h at 150° C., a colorless precipitate forming. The mixture was then allowed to cool to 20° C., hydrolyzed with 80 ml of 2 N hydrochloric acid (pH 1) and stirred for 15 min and the organic phase separated. The organic phase was washed with 30 ml of saturated sodium bicarbonate solution. After phase separation, drying was effected over sodium sulfate and the solvent was distilled off under reduced pressure (>90% of the solvent was recovered). 1-phenylhexan-3-one was obtained in a yield of 13.6 g (91% of theory) with a boiling point of 134° C. (13 mbar).

Provenance & Evidence