Hexanoic Acid → N-Hydroxysuccinimide caproic acid ester

HRID 2273686Notes

Reaction equation

HRID 2273686 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]>C1COCC1>[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

4

Reactant 2

HCID 8892Hexanoic AcidHCID 80170N-Hydroxysuccinimide

Product 1

HCID 152438N-Hydroxysuccinimide caproic acid esterYield 87.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 55.2 g (0.475 mol) of hexanoic acid and 60.161 g (0.523 mol) of N-hydroxy succinimide in 600 mL THF, 107.855 g (0.523 mol) of DCCl 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 THF solvent was removed by vacuum rotary evaporation. The yellow oil residue was dissolved again in 600 mL hexane followed by another vacuum filtration to remove the excess dicyclohexyl urea (DCU). The filtrate was then concentrated under vacuum evaporation yield a white solid, which was vacuum dried at ambient temperature to give 88.187 g (87.07%) 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. temperatureThe mixture was cooled with an ice-water bath
  2. customThe dicyclohexyl urea (DCU) precipitate was removed by filtration
  3. customthe THF solvent was removed by vacuum rotary evaporation
  4. dissolutionThe yellow oil residue was dissolved again in 600 mL hexane
  5. filtrationfollowed by another vacuum filtration
  6. customto remove the excess dicyclohexyl urea (DCU)
  7. concentrationThe filtrate was then concentrated under vacuum evaporation
  8. customyield a white solid, which
  9. customdried at ambient temperature

Sources & evidence

ORD record
ord-38856a898fca462fad0337c61e3ec2eb
Source dataset
uspto-grants-2015_09
Patent number
US09125969B2

Reaction notes

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