1,2-Dichloroethane → (2R)-2-(Phenoxymethyl)oxirane

HRID 915536Notes

Reaction equation

HRID 915536 reaction equation
[CH2:1]([C@H:3]1[O:5][CH2:4]1)Cl.ClCCCl.[C:10]1([OH:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH-].[Na+]>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.O>[CH2:1]([O:16][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C@@H:3]1[O:5][CH2:4]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 996PhenolHCID 14798Sodium HydroxideHCID 149428(+)-Epichlorohydrin

Product 1

HCID 1534344(2R)-2-(Phenoxymethyl)oxiraneYield 80%

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 (36 mg), 1,2-dichloroethane (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 (4.10 g, 25 mmol) was dropped in a ten minute period under stirring. The mixture was stirred for 30 minutes under ice-cooling and then for 42 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 (2.27 g, yield 80%, 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-3791f899e0b54655994e417b1027772e
Source dataset
uspto-grants-2007_09
Patent number
US07265232B2

Reaction notes

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