Maleic Anhydride → 6-Maleimido-1-hexanol

HRID 2306122Notes

Reaction equation

HRID 2306122 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=O)[CH:3]=[CH:2]1.[NH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15]>C(O)(=O)C>[OH:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][N:8]1[C:1](=[O:7])[CH:2]=[CH:3][C:4]1=[O:6]

Participants

4

Reactant 2

HCID 7923Maleic AnhydrideHCID 199606-Amino-1-hexanol

Product 1

HCID 121937996-Maleimido-1-hexanol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

One mole equivalent of maleic anhydride and one mole equivalent of 6-amino hexanol are dissolved in anhydrous acetic acid and the solution is heated under reflux for eight hours. The acetic acid is distilled off in a rotary evaporator. The residue is dissolved in diethyl ether and washed once with 1 N NaOH, and twice with water. After drying over MgSO4 and evaporating the diethyl ether, the residue is crystallized from isopropyl ether to produce N-(6-hydroxyhexyl) maleimide.

Workup

  1. temperaturethe solution is heated
  2. temperatureunder reflux for eight hours
  3. distillationThe acetic acid is distilled off in a rotary evaporator
  4. dissolutionThe residue is dissolved in diethyl ether
  5. washwashed once with 1 N NaOH
  6. dry with materialAfter drying over MgSO4
  7. customevaporating the diethyl ether
  8. customthe residue is crystallized from isopropyl ether

Sources & evidence

ORD record
ord-55e5aa71184643d3a2b45f40104d61bb
Source dataset
uspto-grants-2002_08
Patent number
US06441213B1

Reaction notes

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