Dicyclohexylcarbodiimide → N-[(E,E)-4-ethyl-2,4-hexadienoyloxy]succinimide

HRID 35572Notes

Reaction equation

HRID 35572 reaction equation
[CH2:1](/[C:3](=[CH:9]\[CH3:10])/[CH:4]=[CH:5]/[C:6]([OH:8])=[O:7])[CH3:2].O[N:12]1[C:16](=[O:17])[CH2:15][CH2:14][C:13]1=[O:18].C1(N=C=NC2CCCCC2)CCCCC1>O1CCOCC1>[CH2:9](/[C:3](=[CH:1]\[CH3:2])/[CH:4]=[CH:5]/[C:6]([O:8][N:12]1[C:16](=[O:17])[CH2:15][CH2:14][C:13]1=[O:18])=[O:7])[CH3:10]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 109425234-Ethylhexa-2,4-dienoic acid

Product 1

HCID 14329790N-[(E,E)-4-ethyl-2,4-hexadienoyloxy]succinimideYield 90.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of (E,E)-4-ethyl-2,4-hexadienoic acid (7 g) and N-hydroxysuccinimide (5.75 g) in dioxane (100 ml) was added dicyclohexylcarbodiimide (10.8 g). The mixture was stirred at ambient temperature overnight and then filtered. The filtrate was concentrated under reduced pressure to give a residue which was recrystallized from a mixture of ether and petroleum ether to give N-[(E,E)-4-ethyl-2,4-hexadienoyloxy]succinimide (10.73 g).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customto give a residue which
  4. customwas recrystallized from a mixture of ether and petroleum ether

Sources & evidence

ORD record
ord-38ad3984fcb74f87b3d3430852c37cf5
Source dataset
uspto-grants-1988_08
Patent number
US04767768

Reaction notes

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