Sodium Hydroxide → 1-Phenylhexan-3-one

Participants

Reaction Conditions

Reaction Steps

8.5 g of sodium hydroxide prills (213 mmol) in 100 ml of polyethylene glycol 1000 dimethyl ether (m.p.: 42° C.) were initially introduced at room temperature into a 3-necked flask having a dropping funnel, internal thermometer and stirrer. After 25 g of 3-hydroxy-3-(2′-phenylethyl)hexanoic acid (106 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 80° C. for 10 min and then to 150° C. Thereafter, the pressure was reduced to 2.5 mbar and the mixture was stirred for 2 h at 150° C. and a pressure of 2.5 mbar, 1-phenylhexan-3-one formed by cleavage being collected in a cooled receiver. The 1-phenylhexan-3-one collected in the receiver was obtained, after washing with 20 ml of water, in a yield of 12.1 g (81% of theory) with a boiling point of 133° C. (13 mbar).

Provenance & Evidence