(-)-Epichlorohydrin → HCID 53485842, compound

HRID 720749Notes

Reaction equation

HRID 720749 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-8817d890975543579e7e568b93d3e6ea
Source dataset
uspto-grants-2006_11
Patent number
US07135576B2

Reaction notes

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