Phenol → (2R)-2-(Phenoxymethyl)oxirane

HRID 915535Notes

Reaction equation

HRID 915535 reaction equation
[CH2:1]([C@H:3]1[O:5][CH2:4]1)Cl.C1(C)C=CC=CC=1.[C:13]1([OH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+]>O>[CH2:1]([O:19][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C@@H:3]1[O:5][CH2:4]1

Participants

6

Reactant 4

HCID 996PhenolHCID 1140TolueneHCID 14798Sodium HydroxideHCID 149428(+)-Epichlorohydrin

Product 1

HCID 1534344(2R)-2-(Phenoxymethyl)oxiraneYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a reaction vessel were added (S)-epichlorohydrin (99% ee, 2.64 g, 29 mmol), toluene (6 ml) and water (6 ml), and the mixture was cooled with ice. After adding phenol (1.78 g, 19 mmol), thereto 24% aqueous NaOH solution (4.75 g, 29 mmol) was dropped under stirring over a ten minute period. The mixture was stirred for 30 minutes under ice-cooling and then for 50 hours at room temperature. The aqueous layer was removed and the organic layer was neutralized with 5% HCl and washed with water twice. The solvent was removed to give objective crude (R)-glycidylphenyl ether (1.96 g, yield 69%, optical purity 98% ee) as an oil.

Workup

  1. temperaturethe mixture was cooled with ice
  2. stirringThe mixture was stirred for 30 minutes under ice-
  3. temperaturecooling
  4. customThe aqueous layer was removed
  5. washwashed with water twice
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-9e8362f6b00f400d9580372a72d6ed88
Source dataset
uspto-grants-2007_09
Patent number
US07265232B2

Reaction notes

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