Formaldehyde → 4,5,6,7-Tetrabromo-2-(hydroxymethyl)-1H-isoindole-1,3(2H)-dione

HRID 1415107Notes

Reaction equation

HRID 1415107 reaction equation
[Br:1][C:2]1[C:3]([Br:15])=[C:4]([Br:14])[C:5]([Br:13])=[C:6]2[C:11](=[O:12])[NH:10][C:8](=[O:9])[C:7]=12.[CH2:16]=[O:17]>C(O)C>[CH2:16]([N:10]1[C:11](=[O:12])[C:6]2=[C:5]([Br:13])[C:4]([Br:14])=[C:3]([Br:15])[C:2]([Br:1])=[C:7]2[C:8]1=[O:9])[OH:17]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 904903,4,5,6-Tetrabromophthalimide

Product 1

HCID 217110024,5,6,7-Tetrabromo-2-(hydroxymethyl)-1H-isoindole-1,3(2H)-dioneYield 87.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

Tetrabromophthalimide (30 gm) was suspended in 100 ml of ethanol and 50 gm of 38 percent formaldehyde was added. Then the solution was stirred and heated for three hours at 85° C. Upon cooling, the product was filtered yielding 28 gm of a white solid having a melting point greater than 350° C. The infrared spectrum of the product showed the disappearance of the imide NH and the appearance of an OH absorption at 3450 cm-1. Analysis: Calculated for C9H3Br4NO3 ; Br, 64.8; hydroxyl number: 89.0; Found: Br, 63.28; hydroxyl number: 90.45.

Workup

  1. temperatureUpon cooling
  2. filtrationthe product was filtered

Sources & evidence

ORD record
ord-d74422b938bb480aaab98cfd5e7e545a
Source dataset
uspto-grants-1977_01
Patent number
US04003862

Reaction notes

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