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

HRID 868220Notes

Reaction equation

HRID 868220 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-4bd14eaa85e24b5ca56a4edcaf78dbc7
Source dataset
uspto-grants-1988_10
Patent number
US04778804

Reaction notes

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