Formaldehyde → 3-(Hydroxymethyl)-1H-pyrrole-2,5-dione

HRID 10604

Reaction equation

HRID 10604 reaction equation
[C:1]1(=[O:7])[NH:5][C:4](=[O:6])[CH:3]=[CH:2]1.[CH2:8]=[O:9].[OH-].[Na+]>>[OH:9][CH2:8][C:2]1[C:1]([NH:5][C:4](=[O:6])[CH:3]=1)=[O:7]

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 10935MaleimideHCID 14798Sodium Hydroxide

Product 1

HCID 219817513-(Hydroxymethyl)-1H-pyrrole-2,5-dione

Procedure

24 Parts of maleimide (manufactured by Aldrich Corporation), 21 parts of 35% HCOH (manufactured by Wako Pure Chemical Industries, Ltd.) and 0.7 parts of a 5% aqueous NaOH solution are placed in a reactor and reacted at 40° C. for 2 hours. As a result, a white crystal of hydroxymethylmaleimide precipitates. This white crystal is filtered under reduced pressure and then dried at normal temperature under vacuum. The crude crystal of hydroxymethylmaleimide obtained in this manner is recrystallized from ethyl acetate to obtain 22 parts of hydroxymethylmaleimide.

Workup

  1. customreacted at 40° C. for 2 hours
  2. customAs a result, a white crystal of hydroxymethylmaleimide precipitates
  3. filtrationThis white crystal is filtered under reduced pressure
  4. customdried at normal temperature under vacuum

Sources & evidence

ORD record
ord-9a2925c670fe42288d32beb72b10d9f5
Source dataset
uspto-grants-2006_08
Patent number
US07094860B2

Linked notes

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