Benzyl Bromide → p-(Benzyloxy)phenethyl alcohol

HRID 490065Notes

Reaction equation

HRID 490065 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)C>[CH2:17]([O:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][OH:1])=[CH:5][CH:6]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10393TyrosolHCID 11430Potassium Carbonate

Product 1

HCID 3017260p-(Benzyloxy)phenethyl alcohol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-(2-hydroxy-ethyl)-phenol (50 g, 0.36 mol) in ethanol (400 ml) is added potassium carbonate (75 g, 0.54 mol, 1.5 eq) and benzyl bromide (47.2 ml, 0.39 mol, 1.1 eq), the reaction mixture is stirred at room temperature overnight. The reaction mixture is then filtered off trough celite and concentrated under vacuum. 2-(4-Benzyloxy-phenyl)-ethanol is isolated after crystallization with diethyl ether (82.6 g, 95%).

Workup

  1. filtrationThe reaction mixture is then filtered off trough celite
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ad32d45293da40d0913a57adb51923e1
Source dataset
uspto-grants-2009_05
Patent number
US07528120B2

Reaction notes

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