(-)-Epichlorohydrin → HCID 53485842, compound

HRID 1814226Notes

Reaction equation

HRID 1814226 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].[CH2:13]([C@@H:15]1[O:17][CH2:16]1)Cl>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.CO>[CH2:13]([C:10]1[CH:9]=[CH:8][CH:7]=[C:3]2[C:4]([NH:5][C:1](=[O:11])[C:2]=12)=[O:6])[C@H:15]1[O:17][CH2:16]1

Participants

5

Reactant 2

HCID 2734062(-)-EpichlorohydrinHCID 24194345Phthalimide potassium salt

Product 1

HCID 53485842HCID 53485842, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

Into a reaction vessel were put potassium phthalimide (5.00 g, 27.0 mmol), benzyltrimethylammonium chloride (0.50 g, 2.70 mmol) and methanol (50 ml) and then thereto was added (R)-epichlorohydrin (9.99 g, 81.0 mmol). The mixture was stirred at 20° C. for 15 hours and the solvent was removed. To the residue was added ethyl acetate (30 ml), the mixture was washed with water (20 ml) and ethyl acetate was removed to give crude (R)-glycidylphthalimide (3.74 g, yield: 68%, optical purity: 99% e.e.) as a white solid.

Workup

  1. customInto a reaction vessel were put
  2. customthe solvent was removed
  3. additionTo the residue was added ethyl acetate (30 ml)
  4. washthe mixture was washed with water (20 ml) and ethyl acetate
  5. customwas removed

Sources & evidence

ORD record
ord-2f37ad35c0824bc0afed5fe7e04dd756
Source dataset
uspto-grants-2005_04
Patent number
US06875875B2

Reaction notes

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