Reaction #6700

Reaction equation

4-Benzyloxybenzyl chloride

triphenyl phosphine

ether

→

4-benzyloxybenzyltriphenyl phosphonium chloride

Solvents

toluene

Conditions

Workup

1. 1
   FiltrationThe precipitated phosphonium salt was collected by filtration
2. 2
   Washrinsed with ether and air
3. 3
   Otherdried

Procedure

4-Benzyloxybenzyl chloride (1 g, 0.0043 mol) and triphenyl phosphine (1.127 g, 1 equivalent) in anhydrous toluene (20 mL) were refluxed under nitrogen for ˜8–10 hours. A white precipitate appeared in the reaction mixture. The reaction mixture was then cooled to room temperature and ether (100 mL) was added. The precipitated phosphonium salt was collected by filtration, rinsed with ether and air dried. Yield=0.55 g (25%). MALDI-TOF MS 459.51 obs. (459.54 calc.).

Source