Phenol → 1-Benzyl-4-phenoxymethylpiperidine

Participants

Reaction Steps

0.3 g (0.00146 mol) 1-benzyl-4-hydroxymethyl-piperidine, 0.137 g (0.00146 mol) of phenol and 0.45 g (0.0017 mol) of triphenylphosphine were dissolved in 10 ml of toluene, cooled to 10° and treated slowly with 0.264 ml (0.0017 mol) of diethyl azodicarboxylate. The mixture was stirred at 90° for 25 hrs. The solvent was removed, the residue was taken up in ethyl acetate, washed three times with 40 ml of water each time and three times with 40 ml of 2N aqueous NaOH each time and the organic phase was dried over magnesium sulfate. The solvent was removed. The residue was chromatographed on silica gel with ethyl acetate/hexane (1:2) as the eluent. 0.17 g (41.4%) 1-benzyl-4-phenoxymethylpiperidine was obtained as white crystals; m.p. 56°-57°.

Provenance & Evidence