2-Phenylbutyric Acid → HCID 10548239, compound

Participants

Reaction Steps

8-Chlorooctoxybenzene (9.1 g, 38 mmol) was added to a stirred solution of 2-phenylbutyric acid (7.48 g, 46 mmol) in trifluoroacetic anhydride (7.5 ml, 52 mmol) and stirring continued for 16 h. The mixture was poured into saturated sodium bicarbonate solution (100 ml), neutralised by addition of sodium bicarbonate, and extracted with ether (2×100 ml). The combined organic extracts were dried (MgSO4) and concentrated in vacuo. The residues were column-chromatographed (silica; eluant 5-10% dichloromethane in petrol) to give the title compound as a colourless oil (11.86 g, 81%). NMR (CDCl3) δ=0.87 (3H,t,J=7.3 Hz), 1.26-1.50 (8H, m), 1.69-1.90 (5H,m), 2.08-2.26 (1H,m), 3.51 (2H,t,J=6.6 Hz), 3.94 (2H,t,J=6.6 Hz), 4.38 (1H,t,J=7.3 Hz), 6.83 (2H,d,J=8.8 Hz), 7.15-7.20 (1H,m), 7.20-7.28 (4H,m), 7.93 (2H,d,J=8.8 Hz). IR (liq, cm-1) 2933, 2858, 1673, 1600, 1574, 1510 MS(Chemical Ionisation)m/e=387 (M+ +1, 10%)

Provenance & Evidence