Hexanoic Acid → N-Hydroxysuccinimide caproic acid ester

HRID 1695081Notes

Reaction equation

HRID 1695081 reaction equation
[C:1]([OH:8])(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].O[N:10]1[C:14](=[O:15])[CH2:13][CH2:12][C:11]1=[O:16].C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[C:1]([O:8][N:10]1[C:14](=[O:15])[CH2:13][CH2:12][C:11]1=[O:16])(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 8892Hexanoic AcidHCID 10868DicyclohexylcarbodiimideHCID 80170N-Hydroxysuccinimide

Product 1

HCID 152438N-Hydroxysuccinimide caproic acid esterYield 74.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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 (ν(C═O) of ester), 1745-1786 cm−1 (ν(C═O) of imide). 1H-NMR (DMSO-d6, ppm): 0.86 (3H, —CH3), 1.31 (4H, —(CH2)2CH3), 1.62 (2H, CH2CH2COO—), 2.64 (2H, —CH2COO—), 2.80 (4H, —COCH2CH2CO—).

Workup

  1. additionwas added
  2. temperatureThe mixture was cooled with an ice-water bath
  3. customThe dicyclohexyl urea (DCU) precipitate was removed by filtration
  4. customthe DMF solvent was removed by vacuum rotary evaporation
  5. washThe yellow oil residue was washed with water and hexane
  6. customto yield a white solid, which
  7. customdried at 78° C.

Sources & evidence

ORD record
ord-efdcc89e43b047feb98e5cffc423930c
Source dataset
uspto-grants-2012_04
Patent number
US08163302B2

Reaction notes

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