Triphenylphosphine → (3-Benzyloxypropyl)triphenylphosphonium bromide

Participants

Reaction Steps

A solution of 3-benzyloxy-1-bromopropane (41.0 g., 0.18 mole) and triphenylphosphine (52.4 g., 0.2 mole) in benzene (500 ml.) is stirred and heated at reflux for 92 hours. After removing the solvent in vacuo, the residual gum is dissolved in acetonitrile (50 ml.) providing a pale yellow solution which is diluted with ethyl acetate (400 ml.) to incipient cloudiness and stirred at 25° for 48 hours. Deposited crystals are collected; the yield is 48 g. (53%). Recrystallization from ethyl acetate-acetonitrile (4:1) provides colorless needles, m.p. 151°-152°; pmr (CDCl3)δ2.0 (2H,m), 3.78 (4H,m), 4.49 (2H,s), 7.29 (5H,s) and 7.70 (15H,m).

Provenance & Evidence