Methoxymethyl-triphenylphosphonium chloride → 2-Phenylnaphthalene

Participants

Reaction Steps

In an atmosphere of argon, 823 g (2.40 mol) of (methoxymethyl)triphenylphosphonium chloride and 4 L of dehydrated diethyl ether were charged in a flask. Then, 2.4 L (2.40 mol) of a THF solution of 1M potassium-t-butoxide was added, and the resultant was stirred for 2 hours at room temperature. Then, 6 L of a THF dispersion of 370 g (961 mmol) of 2-(3-formylbiphenyl-4-yl)-6-phenylnapthalene was added dropwise, followed by stirring at room temperature for 17 hours. After the reaction, undissolved matters were filtered, and a filtrate was concentrated. Residues were purified by silica gel chromatography, whereby 330 g of 2-[3-(2-methoxy)ethenyl-1-yl]biphenyl-4-yl]-6-phenylnaphthalene (yield: 83%) was obtained.

Provenance & Evidence