(-)-Epichlorohydrin → HCID 53485842, compound

HRID 720747Notes

Reaction equation

HRID 720747 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>[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 83.1%

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 3776IsopropanolSolvent

Procedure

Into a reaction vessel were put potassium phthalimide (50.0 g, 0.27 mol), benzyltrimethylammonium chloride 5.00 g, 0.027 mol) and isopropanol (500 ml), and the mixture was cooled to 10° C. Thereto was added (R)-epichlorohydrin (74.9 g, 0.81 mol) and the mixture was stirred for 46 hours while being cooled. The solvent was removed and to the residue was added ethyl acetate (250 ml). The mixture was washed with water (250 ml), and then ethyl acetate was removed to give crude (R)-glycidylphthalimide (optical purity: 97% e.e.). The crude product was crystallized from ethyl acetate-hexane to give the object (R)-glycidylphthalimide (45.6 g, yield: 83%, optical purity: 98% e.e.) as white crystals. mp 100–102° C.

Workup

  1. customInto a reaction vessel were put
  2. temperaturewhile being cooled
  3. customThe solvent was removed and to the residue
  4. additionwas added ethyl acetate (250 ml)
  5. washThe mixture was washed with water (250 ml)
  6. customethyl acetate was removed
  7. customto give crude (R)-glycidylphthalimide (optical purity: 97% e.e.)
  8. customThe crude product was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-5d3388867f3246848507850e5c21f890
Source dataset
uspto-grants-2006_11
Patent number
US07135576B2

Reaction notes

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