Benzyl Bromide → 2-(3-Benzyloxyphenoxy)ethanol

HRID 393359Notes

Reaction equation

HRID 393359 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:11]=[CH:10][CH:9]=[C:7]([OH:8])[CH:6]=1.[OH-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CO>[CH2:14]([O:8][C:7]1[CH:6]=[C:5]([CH:11]=[CH:10][CH:9]=1)[O:4][CH2:3][CH2:2][OH:1])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 152273Phenol, 3-(2-hydroxyethoxy)-

Product 1

HCID 121470482-(3-Benzyloxyphenoxy)ethanolYield 79.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of O-(2-Hydroxyethyl)resorcinol (4 g) and sodium hydroxide (1.04 g) dissolved in methanol (60 mL) was added benzyl bromide (4.44 g), and the resulting reaction mixture was stirred overnight. After this time, approximately 30 mL of the methanol was removed in vacuo, and the mixture was diluted with methylene chloride (100 mL). The organics were washed with water and aqueous 1N NaOH, dried, and concentrated to provide 2-(3-benzyloxyphenoxy)ethanol (5.03 g).

Workup

  1. customthe resulting reaction mixture
  2. customAfter this time, approximately 30 mL of the methanol was removed in vacuo
  3. additionthe mixture was diluted with methylene chloride (100 mL)
  4. washThe organics were washed with water and aqueous 1N NaOH
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-39e70c5d47ff499eb457287233bf9d7b
Source dataset
uspto-grants-2004_10
Patent number
US06806369B2

Reaction notes

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