2,4,6-Trimethylbenzyl chloride → Phthalimide

HRID 1956706Notes

Reaction equation

HRID 1956706 reaction equation
CC1C=C(C)C=C(C)C=1CCl.[C:12]1(=[O:22])[NH:16][C:15](=[O:17])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12.[K]>CN(C)C=O>[C:12]1(=[O:22])[NH:16][C:15](=[O:17])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12

Participants

4

Reactant 2

HCID 741082,4,6-Trimethylbenzyl chlorideHCID 24194345Phthalimide potassium salt

Product 1

HCID 6809PhthalimideYield 115.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N-Dimethylformamide (50 mL), 2,4,6-trimethylbenzyl chloride (5.06 g, 30 mmol) and potassium phthalimide (6.11 g, 33 mmol) were combined with stirring. After an initial reaction temperature rise from approximately 25° C. to 34° C. during 15 minutes, the temperature receded to room temperature and stirring was continued for approximately 17 hours. Solvent then was removed and the residue was thoroughly triturated with water and dried. The 7.62 g crude product was recrystallized from ethyl acetate and dried to yield 5.62 g of white phthalimide: mp 204.5°-206.5° C. (softens 196.5° C.) (lit. mp 209.5°-210° C. (R. T. Fuson and J. J. Denton, J. Am. Chem. Soc., 63, 654 (1941))); 1H NMR (DMSO-d6) δ7.82 (s, 4H), 6.78 (s, 2H), 4.72 (s, 2H), 2.28 (s, 6H), 2.17 (s, 3H). IR(KBr): 1765, 1710 cm-1 ; MS (m/z) 279 (M+).

Workup

  1. customAfter an initial reaction temperature rise from approximately 25° C. to 34° C. during 15 minutes
  2. customreceded to room temperature
  3. stirringstirring
  4. customSolvent then was removed
  5. customthe residue was thoroughly triturated with water
  6. customdried
  7. customThe 7.62 g crude product was recrystallized from ethyl acetate
  8. customdried

Sources & evidence

ORD record
ord-7d4cac9e2c294e04ada62ea70a13298a
Source dataset
uspto-grants-1998_07
Patent number
US05780505

Reaction notes

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