p-Toluenesulfonic acid → Acetic acid, (dimethoxyphosphinyl)hydroxy-, (4-nitrophenyl)methyl ester

HRID 1290392Notes

Reaction equation

HRID 1290392 reaction equation
[C:1]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)(=[O:4])[CH:2]=[O:3].[CH3:16][O:17][P:18]([O-:21])[O:19][CH3:20].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[N+:13]([C:10]1[CH:11]=[CH:12][C:7]([CH2:6][O:5][C:1](=[O:4])[CH:2]([P:18]([O:19][CH3:20])([O:17][CH3:16])=[O:21])[OH:3])=[CH:8][CH:9]=1)([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 12544839(4-Nitrophenyl)methyl oxoacetateHCID 21884954Dimethylphosphite

Product 1

HCID 10064522Acetic acid, (dimethoxyphosphinyl)hydroxy-, (4-nitrophenyl)methyl ester

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a mixture of 4.32 g of p-nitrobenzyl glyoxalate and 2.0 ml of dimethylphosphite in 25 ml of benzene is added a catalytic amount of p-toluenesulfonic acid. The reaction is heated at reflux temperature for 1.5 hours. The formed water is removed using a Dean-Stark trap. After cooling, the solvent is removed in vacuo and the resulting crystals are slurried in ethyl acetate and collected to give 3.48 g of the desired product.

Workup

  1. temperatureThe reaction is heated
  2. temperatureat reflux temperature for 1.5 hours
  3. customThe formed water is removed
  4. temperatureAfter cooling
  5. customthe solvent is removed in vacuo
  6. customcollected

Sources & evidence

ORD record
ord-caeb0547645f4115872e20be72f7dda2
Source dataset
uspto-grants-1998_05
Patent number
US05750735

Reaction notes

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