Toluene → HCID 13143164, compound

HRID 1449375Notes

Reaction equation

HRID 1449375 reaction equation
[CH2:1]([O:3][P:4](C=C)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[C]=[O:12].[H][H].[C:15]1([CH3:21])[CH:20]=CC=CC=1>[Rh]>[CH2:1]([O:3][P:4]([CH:15]([CH:20]=[O:12])[CH3:21])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

6

Reactant 4

HCID 1140TolueneHCID 69629Diethyl vinylphosphonateHCID 178418361HCID 178418361, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 13143164HCID 13143164, compound

Reagents, catalysts & solvents 1

HCID 23948RhodiumCatalyst

Procedure

In a 1 liter autoclave equipped with an electromagnetic reciprocating stirrer, 228 g of vinylphosphonic acid diethyl ester and 100 ppm of rhodium as dimeric cyclooctadien-1,5-yl rhodium chloride in 600 ml of toluene as solvent are heated at 80° C. and reacted under a pressure of 600 bars with a mixture of carbon monoxide and hydrogen in a ratio of 1:1. The pressure is maintained for 12 hours by topping up with the gas mixture. The contents are allowed to cool before the pressure on the autoclave is released. The reaction mixture is worked up by distillation. There is obtained 191 g of α-formylethanephosphonic acid diethyl ester; b.p.: 113° C./11 mm Hg.

Workup

  1. customIn a 1 liter autoclave equipped with an electromagnetic reciprocating stirrer
  2. temperatureThe pressure is maintained for 12 hours
  3. temperatureto cool before the pressure on the autoclave
  4. distillationThe reaction mixture is worked up by distillation

Sources & evidence

ORD record
ord-334ef4bd28d44944a70c3c63fbceab3a
Source dataset
uspto-grants-1980_02
Patent number
US04190650

Reaction notes

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