Phenol → (2R, 3S)-3-phenoxy-3-phenylpropane-1,2-diol

HRID 351913Notes

Reaction equation

HRID 351913 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[CH:10]1[CH:15]=[CH:14][C:13]([C@H:16]2[O:18][C@@H:17]2[CH2:19][OH:20])=[CH:12][CH:11]=1>O>[O:7]([C@@H:16]([C:13]1[CH:14]=[CH:15][CH:10]=[CH:11][CH:12]=1)[C@H:17]([OH:18])[CH2:19][OH:20])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 14798Sodium Hydroxide2×HCID 150502((2R,3R)-3-phenyloxiran-2-yl)methanol

Product 1

HCID 59886004(2R, 3S)-3-phenoxy-3-phenylpropane-1,2-diolYield 38.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of phenol (9.4 g), NaOH (1.33 g) and water (6.6 ml) was heated on a boiling water bath until the mixture became homogeneous. (2R, 3R)-3-Phenylglycidol (5.0 g) was added in small portions over a period of 10 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 (3.99 g) in ice water (75 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 white solid. Recrystallization from methylene chloride gave white crystals (3.1 g) of (2R, 3S)-3-phenoxy-3-phenylpropane-1,2-diol.

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 white solid
  7. customRecrystallization from methylene chloride

Sources & evidence

ORD record
ord-f6dd6b3cf32641be9af41215168c0fe4
Source dataset
uspto-grants-2004_06
Patent number
US06743820B2

Reaction notes

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