Benzaldehyde, 4-(phenylmethoxy)- → HCID 54204380, compound

Participants

Reaction Steps

A solution of n-butyllithium in hexane (1.6 M, 20 ml) was added to a stirred suspension of finely powdered [3-(1-methoxy-1-methylethoxy)propyl] triphenylphosphonium bromide (14 g) in dry THF (100 ml) at 0°. The mixture was stirred at 0° for 30 min, treated with a solution of 4-(phenylmethoxy)benzaldehyde (5 g) in THF (25 ml), stirred at 0° for 2 h and filtered through silica. The filtercake was washed with ER, the combined filtrates evaporated in vacuo and the residual oil triturated with ER (50 ml) and filtered through silica. The filtrate was evaporated and the residue dissolved in THF-water-2 M hydrochloric acid (50:5:1, 56 ml) and kept at 23° for 20 min. The mixture was diluted with water (200 ml), extracted with ER (200 ml) and the extract was washed with water (100 ml), brine (50 ml) dried and evaporated to give a white solid which was stirred in hexane and filtered to give the title alcohol (5.2 g) m.p. 93°-95°.

Provenance & Evidence