Formaldehyde → N-Methylolmaleimide

HRID 544184Notes

Reaction equation

HRID 544184 reaction equation
[CH2:1]=[O:2].[C:3]1(=[O:9])[NH:7][C:6](=[O:8])[CH:5]=[CH:4]1>C(=O)([O-])[O-].[K+].[K+].O>[OH:2][CH2:1][N:7]1[C:6](=[O:8])[CH:5]=[CH:4][C:3]1=[O:9]

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 10935Maleimide

Product 1

HCID 227678N-Methylolmaleimide

Reagents, catalysts & solvents 2

HCID 11430Potassium CarbonateCatalystHCID 962WaterSolvent

Procedure

A mixture of 125 grams of water, 26 ml. of 37% aqueous formaldehyde solution, 25 grams of maleimide, and 0.1 gram of anhydrous potassium carbonate was heated at its reflux temperature for 90 minutes, cooled to ambient temperature, and filtered. After removal of the water by heating under vacuum, there was obtained 32 grams of N-hydroxymethylmaleimide.

Workup

  1. temperaturereflux temperature for 90 minutes
  2. filtrationfiltered
  3. customAfter removal of the water
  4. temperatureby heating under vacuum

Sources & evidence

ORD record
ord-518a30de814841f19891fd994498d113
Source dataset
uspto-grants-1984_05
Patent number
US04448906

Reaction notes

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