Benzyl Bromide → p-(Benzyloxy)phenethyl alcohol

HRID 1433329Notes

Reaction equation

HRID 1433329 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 through celite and concentrated under vacuum. 2-(4-Benzyloxy-phenyl)-ethanol is isolated after crystallization with diethyl ether.

Workup

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

Sources & evidence

ORD record
ord-e58c9bc51e9c48e99320cb866d0c6e7d
Source dataset
uspto-grants-2009_11
Patent number
US07612238B2

Reaction notes

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