2,4,6-Trimethylbenzyl chloride → Phthalimide

Participants

Reaction Steps

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+).

Provenance & Evidence