Diethyl Ether → p-(Benzyloxy)phenethyl alcohol

HRID 1488335Notes

Reaction equation

HRID 1488335 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1.[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].CCOCC>CC(C)=O.O>[CH2:11]([O:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][CH2:7][OH:8])=[CH:4][CH:3]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 7498Benzyl BromideHCID 10393TyrosolHCID 11430Potassium Carbonate

Product 1

HCID 3017260p-(Benzyloxy)phenethyl alcohol

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A mixture of 4-hydroxyphenethyl alcohol (15.02 g), benzyl bromide (13.6 ml), and potassium carbonate (75.1 g) in acetone (250 ml) is heated at reflux for about 4 hours. The mixture is cooled and poured into ether and water. The organic layer is washed with water, 1N sodium hydroxide solution, brine, dried over magnesium sulfate, filtered and concentrated in vacuo to give 4-benzyloxyphenethyl alcohol.

Workup

  1. temperatureis heated
  2. temperatureat reflux for about 4 hours
  3. temperatureThe mixture is cooled
  4. washThe organic layer is washed with water, 1N sodium hydroxide solution, brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b2691b85c0e342e2a1caeac5db949915
Source dataset
uspto-grants-1997_10
Patent number
US05674482

Reaction notes

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