Benzaldehyde → HCID 53688132, compound

Participants

Reaction Steps

To a stirred solution of 4-Methyl-2-(diethylphosphono) pentanoic acid methyl ester (25.72 g, 96.3 mmole) in dry tetrahydrofuran (250 ml) under nitrogen was added sodium hydride (4.2 g, 60% dispersion in oil) portionwise. After stirring for 30 min. at room temperature benzaldehyde (11.22 g, 96.3 mmole) was slowly added and the reaction mixture was then stirred for a further hour at room temperature. Volatiles were then removed in vacuo and the residue was dissolved in ethyl acetate, washed with saturated aqueous ammonium chloride solution (250 ml×2), dried (sodium sulphate), filtered and evaporated in vacuo to an oil. Distillation under reduced pressure gave the title compound as an oil (16.6 g, 79%); (Found: C, 75.83; H, 8.38. C14H18O2 +0.2H2O requires: C, 75.78; H, 8.36%); δ(CDCl3) 0.87 and 0.95 (together 6H, each d, each J=7 Hz, (CH3)2CH); 1.90 (1H, m, (CH3)2CH); 2.34 and 2.52 (together 2H, each d, each J=8 Hz, CH2CH(CH3 )2); 3.82 (3H, s, OCH3); 7.70 and 7.2-7.42 (together 6H, s, m, C6H5, vinyl CH).

Provenance & Evidence