Formaldehyde → NSC231616

HRID 1248164Notes

Reaction equation

HRID 1248164 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:6][N:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:4][C:3]1=[O:13].[CH2:15]=[O:16].C1(C)C=CC=CC=1>C(O)(=O)C>[CH3:1][C:2]1([CH3:14])[CH2:6][N:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:4]([CH2:15][OH:16])[C:3]1=[O:13]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 1140TolueneHCID 758614,4-Dimethyl-1-phenyl-3-pyrazolidone

Product 1

HCID 314306NSC231616

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4,4-Dimethyl-1-phenyl-3-pyrazolidone (152 g) was dissolved in 600 ml of acetic acid. To the solution as prepared above, 97 g of an aqueous solution containing 37% of formaldehyde was dropped with stirring at room temperature. The resultant mixture was stirred for 2 hours. At the end of the time, the solvent was distilled away under reduced pressure. To the residue thus obtained, 100 ml of toluene was added, and water was separated at the toluene azeotrope under reduced pressure. A mixture of 900 ml of hexane and 700 ml of ethyl acetate was added to the residue as obtained above which was then dissolved therein by heating. The resultant solution was allowed to cool to room temperature. Crystals precipitated were collected by filtration to obtain 120 g of 4,4-dimethyl-2-hydroxymethyl-1-phenyl-3-pyrazolidone.

Workup

  1. additionwas dropped
  2. distillationAt the end of the time, the solvent was distilled away under reduced pressure
  3. customTo the residue thus obtained
  4. customwater was separated at the toluene azeotrope under reduced pressure
  5. additionA mixture of 900 ml of hexane and 700 ml of ethyl acetate
  6. additionwas added to the residue
  7. customas obtained above which
  8. dissolutionwas then dissolved
  9. temperatureby heating
  10. temperatureto cool to room temperature
  11. customCrystals precipitated
  12. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-da434442b82143ab9800d96fab40c1e9
Source dataset
uspto-grants-1985_06
Patent number
US04522917

Reaction notes

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