HCID 20157919, compound → Methyl 3-{2-[(Z)-1-tridecenyl]phenyl}propanoate

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A solution of methyl 3-[2-(1-tridecynyl)phenyl]propanoate (500 mg) in pyridine (20 ml) was hydrogenated at atmospheric pressure over 5% palladium on barium sulphate (20 mg) until 1 equivalent of hydrogen was absorbed. The catalyst was then removed by filtration and the filtrate evaporated to a pale yellow oil. Chromatograpy on silica eluting with 1:1 dichloromethane-petrol (bp 60°-80° C.) gave 390 mg (78%) of the title ester, νmax (film) 2930, 2850, 1740 cm-1, δ(CDCl3), 0.87 (3H, distorted t, terminal CH3), 1.28 (18H, m, alkylene chain), 2.09 (2H, m, allylic CH2), 2.50 (2H, m, ArCH2), 2.90 (2H, m, CH2CO2), 3.65 (3H, s, ester CH3), 5.70 (1H, d.t, Jd 11.5 Hz, Jt 7.5 Hz, C=CH--R), 6.42 (1H, distorted d, Ar CH=C), 7.17 (4H, m, arom).

Provenance & Evidence