Benzaldehyde → HCID 131726545, compound

Participants

Reaction Steps

Benzaldehyde (6.63 g, 0.062 mol, 6.35 ml) in dry THF (20 ml) was added dropwise to a stirred suspension of NaH (60% dispersion, 5.51 g, 0.138 mol) and (5-carboxyhexyl)-triphenylphosphonium bromide (30 g, 0.066 mol) in dry THF (260 ml). After stirring overnight, the solvent was evaporated to dryness, and the residue taken up into water (300 ml). The solution was made alkaline (pH 12-14) with NaOH solution (4 M) and extracted with EtOAc. The basic solution was then acidified (conc. HCl), extracted with Et2O, and the combined extracts washed with brine and dried with MgSO4. Removal of the solvent afforded 16.5 g of crude product which was purified by chromatography (silica, 1:5 EtOAc/petroleum ether, increasing to 1:1 EtOAc/petroleum ether toward completion) to give 10.81 g (85%) of E-/Z-7-phenylhept-6-ene-oic acid (˜1:1 mixture) as a pale yellow oil. Hydrogenation of the unsaturated acid (10% Pd—C, EtOAc) afforded the saturated compound (51): 1H NMR (CDCl3) δ 11.57 (br s, 1H), 7.20 (m, 5H), 2.58 (t, J=7.7 Hz, 2H), 2.31 (t, J=7.5 Hz, 2H), 1.61 (m, 4H), 1.33 (m, 4H). 13C NMR (CDCl3), δ 180.8, 142.7, 128.5, 128.4, 125.7, 36.0, 34.2, 31.4, 29.0, 24.7.

Provenance & Evidence