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

HRID 915534Notes

Reaction equation

HRID 915534 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+]>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.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

7

Reactant 4

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

Product 1

HCID 1534344(2R)-2-(Phenoxymethyl)oxiraneYield 83%

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

To a reaction vessel were added (S)-epichlorohydrin (99% ee, 30.0 g, 0.32 mol), benzyltrimethylammonium chloride (0.80 g), toluene (70 ml) and water (70 ml), and the mixture was cooled with ice. After addition of phenol (20.3 g, 0.22 mol), thereto 24% aqueous NaOH solution (54.0 g, 0.33 mol) was dropped in a period of one hour under stirring. The mixture was stirred for 30 minutes under ice-cooling and then for 39 hours at room temperature. After the reaction the aqueous layer was removed and the organic layer was neutralized with 5% aqueous HCl solution (70 ml) and washed with water (40 ml). After removal of toluene, the residue was distilled to give objective (R)-glycidylphenyl ether (27.0 g, yield 83%, optical purity 98% ee) as a colorless liquid.

Workup

  1. temperaturethe mixture was cooled with ice
  2. stirringThe mixture was stirred for 30 minutes under ice-
  3. temperaturecooling
  4. customAfter the reaction the aqueous layer
  5. customwas removed
  6. washwashed with water (40 ml)
  7. customAfter removal of toluene
  8. distillationthe residue was distilled

Sources & evidence

ORD record
ord-20ebcbf43017479fa308e8e06e69fa6d
Source dataset
uspto-grants-2007_09
Patent number
US07265232B2

Reaction notes

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