Tritylation of Benzyl Alcohol --- 4-(4-methyl-1-piperidinyl)pyridine (MPP) as Catalyst

  1. To a solution of benzyl alcohol (2.17 g, 0.02 mol), MPP (0.15 g, 0.86 mmol), and triethylamine (7 mL, 0.05 mol) in dichloromethane (40 mL) is added trityl chloride (5.85 g, 0.021 mol).

  2. The reaction mixture is allowed to stand at ambient temperature overnight.

  3. The solvent is removed and the residue crystallized from ethanol (80 mL).  Recrystallization from ethanol affords triphenylmethylbenzyl ether (6.2 g, 87.6%, m.p. 105-106°C).

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Alkylation

Tritylation

Triphenylmethylation

Primary Alcohol

Benzylic Alcohol