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

HRID 748571Notes

Reaction equation

HRID 748571 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

When maleimide (manufactured by Aldrich Chemical Co., Inc.) of 24 parts, 35% HCOH (manufactured by Wako Pure Chemical Industries, Ltd.) of 21 parts, and an aqueous 5% NaOH solution of 0.7 parts are mixed and reacted at 40° C. for 2 hours to precipitate hydroxymethylmaleimide in the form of a white crystal. The produced hydroxymethylmaleimide is filtered in reduced pressure and vacuum dried at room temperature. The crude crystal of hydroxymethylmaleimide obtained in such a manner is recrystallized in ethyl acetate to obtain hydroxymethylmaleimide of 22 parts.

Workup

  1. customreacted at 40° C. for 2 hours
  2. customto precipitate hydroxymethylmaleimide in the form of a white crystal
  3. filtrationThe produced hydroxymethylmaleimide is filtered in reduced pressure and vacuum
  4. customdried at room temperature

Sources & evidence

ORD record
ord-afbf946514684c829070bdb0b279cc09
Source dataset
uspto-grants-2008_07
Patent number
US07399816B2

Reaction notes

Loading…