Formaldehyde → HCID 21266753, compound

HRID 466951Notes

Reaction equation

HRID 466951 reaction equation
C([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[NH:10][C:8](=[O:9])[C:7]2=[CH:13][CH:14]=1)(O)=O.[OH2:15].[CH2:16]=O>CN(C)C=O>[OH:15][CH2:16][C:5]1[CH:4]=[CH:14][CH:13]=[C:7]2[C:8]([NH:10][C:11](=[O:12])[C:6]=12)=[O:9]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 962WaterHCID 88439Trimellitimide

Product 1

HCID 21266753HCID 21266753, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The 4-carboxyphthalimide (0.5 mol) was dissolved in dimethylformamide (200 ml) and H2O (600 ml) and treated with 37% aqueous formaldehyde (100 ml) and the mixture was heated on a steam bath until the solution became homogenous. The reaction was placed in an ice bath and cooled. A white solid crystallized and was collected and washed with cold water. The solid was dissolved in THF and dried with MgSO4 and concentrated to yield 96% of hydroxymethylphthalimide product.

Workup

  1. temperaturethe mixture was heated on a steam bath until the solution
  2. customThe reaction was placed in an ice bath
  3. temperaturecooled
  4. customA white solid crystallized
  5. customwas collected
  6. washwashed with cold water
  7. dissolutionThe solid was dissolved in THF
  8. dry with materialdried with MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-cc46fbddd09e4d6aa4830789eac1bf00
Source dataset
uspto-grants-1992_10
Patent number
US05158865

Reaction notes

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