Formaldehyde → HCID 54450268, compound

HRID 267575Notes

Reaction equation

HRID 267575 reaction equation
[CH2:1]=[O:2].[CH2:3]([O:7][P:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[OH:9])[CH:4]([CH3:6])[CH3:5]>O>[CH2:3]([O:7][P:8]([CH2:1][OH:2])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9])[CH:4]([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 20443377HCID 20443377, compound

Product 1

HCID 54450268HCID 54450268, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

15 g of para-formaldehyde are added, at 70°C and with vigorous agitation, to 100 g (0.505 mole) of benzenephosphonous acid isobutyl ester. Agitation is continued for 1 hour at 75°-90°C. The reaction mixture is then cooled, stirred with water, and the organic phase is separated. The aqueous phase is extracted 2 times with chloroform, and the extract is added to the organic phase. After drying with sodium sulfate, distillation is carried out in a water jet vacuum at an interior temperature of up to 80°C. The residue is distilled in a thin layer evaporator at 0.1 torr and a distillation temperature of 190°C. Subsequently, the distillate is again distilled in a normal distillation apparatus. It is pure hydroxymethyl-phenylphosphinic acid isobutyl ester having a boiling point of 155°C at 0.3 torr.

Workup

  1. temperatureThe reaction mixture is then cooled
  2. customthe organic phase is separated
  3. extractionThe aqueous phase is extracted 2 times with chloroform
  4. additionthe extract is added to the organic phase
  5. dry with materialAfter drying with sodium sulfate, distillation
  6. customup to 80°C
  7. distillationThe residue is distilled in a thin layer evaporator at 0.1 torr
  8. customa distillation temperature of 190°C
  9. distillationSubsequently, the distillate is again distilled in a normal distillation apparatus

Sources & evidence

ORD record
ord-18c52abc51f24f5d921c7195fdab4a03
Source dataset
uspto-grants-1976_03
Patent number
US03943170

Reaction notes

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