Maleic Anhydride → 6-Maleimido-1-hexanol
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
Product 1
Reagents, catalysts & solvents 1
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
- temperaturethe solution is heated
- temperatureunder reflux for eight hours
- distillationThe acetic acid is distilled off in a rotary evaporator
- dissolutionThe residue is dissolved in diethyl ether
- washwashed once with 1 N NaOH
- dry with materialAfter drying over MgSO4
- customevaporating the diethyl ether
- 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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