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

HRID 1268087Notes

Reaction equation

HRID 1268087 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 10935Maleimide2×HCID 14798Sodium Hydroxide

Product 1

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

Procedure

Maleimide (10 g, 0.103 mol) was added to 10 mL of a 37% solution of formaldehyde and 0.31 mL of a 5% solution of NaOH was added. Within 10 minutes all of the maleimide had dissolved and an exothermic reaction proceeded. The solution was stirred for 2 hours where white crystals were observed. The solution was placed in a freezer overnight and the resulting crystals filtered and washed with ice cold ethanol and diethyl ether. The white crystals were purified twice by sublimation. See P. O. Tawney, R. H. Snyder, R. P. Conger, K. A. Leibbrand, C. H. Stiteler, and A. R. Williams J. Org. Chem. 26, 15 (1961).m.p. 104-106° C. (9.77 g, 74.6%). 1H-NMR (Acetone-d6, δ, ppm): 4.96 (2H, —CH2—, s), 5.33 (1H, —OH, s), 6.93 (2H, —CH═CH—, s). 13C-NMR (Acetone-d6, δ, ppm): 60.9 (1C, —CH2—), 135.6 (2C, —CH═CH—), 173.1 (1C, —C═O).

Workup

  1. additionwas added
  2. customan exothermic reaction
  3. waitThe solution was placed in a freezer overnight
  4. filtrationthe resulting crystals filtered
  5. washwashed with ice cold ethanol and diethyl ether
  6. customThe white crystals were purified twice by sublimation

Sources & evidence

ORD record
ord-e8dadbe64ca34e76b14221f25563d60a
Source dataset
uspto-grants-2003_04
Patent number
US06555593B1

Reaction notes

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