(+)-Epichlorohydrin → HCID 11608126, compound

HRID 720748Notes

Reaction equation

HRID 720748 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.C(O)(C)(C)C>[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 149428(+)-EpichlorohydrinHCID 24194345Phthalimide potassium salt

Product 1

HCID 11608126HCID 11608126, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 6386tert-ButanolSolvent

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 tert-buyl alcohol (50 ml) and then thereto was added (S)-epichlorohydrin (6.53 g, 54.0 mmol). The mixture was stirred at 20° C. for 24 hours and the solvent was removed. To the residue was added ethyl acetate (30 ml), the mixture was washed with water (20 ml), and then ethyl acetate was removed to give crude (S)-glycidylphthalimide (3.95 g, yield: 72%, optical purity: 97% 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)
  5. customethyl acetate was removed

Sources & evidence

ORD record
ord-57ebbce2264c4bb6b77ea4beb7739163
Source dataset
uspto-grants-2006_11
Patent number
US07135576B2

Reaction notes

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