Reaction #74881

Reaction equation

dimethylmaleic anhydride

4-aminocyclohexanol

→

N-(4-hydroxycyclohexyl)-dimethyl-maleimide

Yield 70.0%

Solvents

methylene chloride

Conditions

Workup

1. 1
   Extractionthe solution is extracted once with 100 ml of 1 N NaOH
2. 2
   Temperaturewhilst cooling with ice
3. 3
   WashThe reaction product is then washed twice with water
4. 4
   Dryingdried over Na2SO4
5. 5
   OtherThe solvent is evaporated
6. 6
   Otherthe residue is recrystallized from a 1:1 mixture by volume of ethyle acetate and petroleum ether

Procedure

126 g (1 mol) of dimethylmaleic anhydride and 115 g (1 mol) of 4-aminocyclohexanol are warmed, whilst stirring, to 120°-125° C. (internal temperature) for 30 minutes in an oil bath. After cooling to about 20° C., the reaction product is dissolved in 500 ml of methylene chloride and the solution is extracted once with 100 ml of 1 N NaOH, whilst cooling with ice. The reaction product is then washed twice with water and dried over Na2SO4. The solvent is evaporated and the residue is recrystallized from a 1:1 mixture by volume of ethyle acetate and petroleum ether. 155 g (70% of theory) of N-(4-hydroxycyclohexyl)-dimethyl-maleimide are obtained; melting point 109°-111° C.

Source