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

HRID 915537Notes

Reaction equation

HRID 915537 reaction equation
[CH2:1]([C@H:3]1[O:5][CH2:4]1)Cl.C(OC)(C)(C)C.[C:12]1([OH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[Na+]>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.O>[CH2:1]([O:18][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C@@H:3]1[O:5][CH2:4]1

Participants

7

Reactant 4

HCID 996PhenolHCID 14798Sodium HydroxideHCID 15413tert-Butyl methyl etherHCID 149428(+)-Epichlorohydrin

Product 1

HCID 1534344(2R)-2-(Phenoxymethyl)oxiraneYield 75%

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

To a reaction vessel were added (S)-epichlorohydrin (99% ee, 2.64 g, 29 mmol), benzyltrimethylammonium chloride (72 mg), tert-butylmethyl ether (6 ml) and water (6 ml), and the mixture was cooled with ice. After addition of phenol (1.78 g, 19 mmol), thereto 24% aqueous NaOH solution (4.75 g, 29 mmol) was dropped in a ten minute period under stirring. The mixture was stirred for 30 minutes under ice-cooling and then for 37 hours at room temperature. After the aqueous layer was removed, the organic layer was neutralized with 5% HCl and washed with water twice. The solvent was removed to give objective crude (R)-glycidylphenyl ether (2.13 g, yield 75%, 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. customAfter the aqueous layer was removed
  5. washwashed with water twice
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-922f8296d24d4ce7aa039f00d707e4c3
Source dataset
uspto-grants-2007_09
Patent number
US07265232B2

Reaction notes

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