Toluene → Phosphonic acid, (1-methyl-2-oxoethyl)-, dimethyl ester

HRID 2049523Notes

Reaction equation

HRID 2049523 reaction equation
[CH3:1][O:2][P:3](C=C)(=[O:6])[O:4][CH3:5].[C]=[O:10].[H][H].[C:13]1([CH3:19])C=CC=C[CH:14]=1>[Rh].C1([Rh](Cl)Cl)CCC=CCCC=1>[CH3:1][O:2][P:3]([CH:13]([CH:14]=[O:10])[CH3:19])(=[O:6])[O:4][CH3:5]

Participants

7

Reactant 4

HCID 1140TolueneHCID 78376Dimethyl vinylphosphonateHCID 178418361HCID 178418361, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 11321161Phosphonic acid, (1-methyl-2-oxoethyl)-, dimethyl ester

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 178479814HCID 178479814, compoundCatalyst

Procedure

In an autoclave of 1 liter capacity, fitted with a magnetic lift-stirrer, 113 g of vinylphosphonic acid dimethyl ester and 100 ppm of rhodium in the form of dimeric cycloocta-1,5-dienyl-rhodium chloride, in 600 ml of toluene as the solvent, are heated at 80° C. and reacted, under a pressure of 600 bars, with a mixture of carbon monoxide and hydrogen in the ratio of 1:1. The pressure is maintained for 12 hours by admitting further gas mixture. The reaction mixture is then allowed to cool under pressure, after which the autoclave is let down. The reaction mixture is worked up by distillation. 91 g of α-formylethane-phosphonic acid dimethyl ester, of boiling point 86°-90° C./0.1 mm Hg, are obtained.

Workup

  1. customIn an autoclave of 1 liter capacity, fitted with a magnetic lift-stirrer
  2. temperatureThe pressure is maintained for 12 hours
  3. temperatureto cool under pressure
  4. distillationThe reaction mixture is worked up by distillation

Sources & evidence

ORD record
ord-3ad5c3c68ce44718acc37d0e10b2c223
Source dataset
uspto-grants-1980_04
Patent number
US04198354

Reaction notes

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