Reaction #1265368

Reaction equation

hexanoic acid

N-hydroxy succinimide

DCCI

→

N-hexanoyloxy succinimide

Yield 74.3%

Solvents

DMF

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   TemperatureThe mixture was cooled with an ice-water bath
3. 3
   OtherThe dicyclohexyl urea (DCU) precipitate was removed by filtration
4. 4
   Otherthe DMF solvent was removed by vacuum rotary evaporation
5. 5
   WashThe yellow oil residue was washed with water and hexane
6. 6
   Otherto yield a white solid, which
7. 7
   Otherdried at 78° C.

Procedure

To a solution of 4.64 g (0.04 mol) of hexanoic acid and 5.75 g (0.05 mol) of N-hydroxy succinimide in 100 mL distilled DMF, 10.3 g (0.05 mol) of DCCI was added. The mixture was cooled with an ice-water bath and stirred for 5 h. The dicyclohexyl urea (DCU) precipitate was removed by filtration, and the DMF solvent was removed by vacuum rotary evaporation. The yellow oil residue was washed with water and hexane to yield a white solid, which was vacuum dried at 78° C. to give 6.34 g (74%) of N-hexanoyloxy succinimide. IR (KBr): 1816 cm−1 (υ(C═O) of ester), 1745–1786 cm−1 (υ(C═O) of imide). 1H-NMR (DMSO-d6, ppm): 0.86 (3 H, —CH3), 1.31 (4H, —(CH2)2CH3), 1.62 (2H, —CH2CH2COO—), 2.64 (2H, —CH2COO—), 2.80 (4H, —COCH2CH2CO—).

Source