Benzenepropanoic acid → 4-Phenylbutyrophenone

Participants

Reaction Conditions

Reaction Steps

A 100 ml flask having a septum cap and magnetic stirrer was initially charged with palladium acetate (67.3 mg, 0.30 mmol), diphenylferrocenylphosphine (194 mg, 0.35 mmol), 3-phenylpropionic acid (1.50 g, 10 mmol) and benzeneboronic acid (1.46 g, 12 mmol). THF (40 ml), water (45 mg, 2.5 mmol) and pivalic anhydride (2.79 g, 15 mmol) were added in succession with the aid of syringes. The reaction vessel was then purged with inert gas and the reaction mixture was heated to 60° C. for a few hours. The progress of the reaction was followed with the aid of gas chromatography. As soon as complete conversion had been attained, the catalyst was removed by filtration through silica gel, the solvent was distilled off and the residue was recrystallized from hexane. The pivalic acid remained in the mother liquor and could be recovered. In this way, 1.73 g (83%) of 3-phenylpropyl phenyl ketone were obtained as colorless crystals. 1H NMR (200 MHz, CDCl3, 25° C., TMS): δ=7.95 (m, 2H), 7.61-7.19 (m, 8H), 3.32 (t, 3J(H,H)=6 Hz, 2H), 3.13 (t, 3J (H,H)=6 Hz, 2H) ppm; 13C NMR (50 MHz, CDCl3, 25° C., TMS): δ=198.8, 141.0, 136.5, 132.7, 128.3, 128.2, 128.1, 127.7, 125.8, 40.1, 29.8 ppm; MS (70 eV): m/z (%): 210(53) [M+], 105(100), 77(46), 51(17), HRMS: calc. for C15H14O [M+]: 210.104465; found: 210.10447; anal. calc. for C15H14O (210.3): C 85.68%; H 6.71%; N 0.00%; found: C 85.37; H 6.67; N 0.00%.

Provenance & Evidence