Phenol → Benzeneethanol, beta-phenoxy-

HRID 351912Notes

Reaction equation

HRID 351912 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[CH2:10]1[O:18][CH:11]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>O>[O:7]([CH:11]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:10][OH:18])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 7276Styrene OxideHCID 14798Sodium Hydroxide2×

Product 1

HCID 565103Benzeneethanol, beta-phenoxy-Yield 30.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of phenol (28.2 g), NaOH (4.0 g) and water (15 ml) was heated on a boiling water bath until the mixture became homogeneous. Styrene oxide (12.0 g) was added dropwise over a period of 15 minutes and the mixture was heated with stirring on a boiling water bath for 1 hr. The mixture was poured into a solution of NaOH (12.0 g) in ice water (200 ml) and extracted with ether (50 ml) 2 times. The ether solution was dried over anhydrous sodium sulfate and the solvent distilled off to obtain a crystalline product. Recrystallization from methylene chloride-hexane gave white crystals (6.6 g) of 2-phenoxy-2-phenylethanol.

Workup

  1. temperaturewas heated on a boiling water bath until the mixture
  2. temperaturethe mixture was heated
  3. extractionextracted with ether (50 ml) 2 times
  4. dry with materialThe ether solution was dried over anhydrous sodium sulfate
  5. distillationthe solvent distilled off
  6. customto obtain a crystalline product
  7. customRecrystallization from methylene chloride-hexane

Sources & evidence

ORD record
ord-1861e77ae3834db6b784970e02edb0dc
Source dataset
uspto-grants-2004_06
Patent number
US06743820B2

Reaction notes

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