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

HRID 1450310

Reaktionsgleichung

Reaktionsgleichung von HRID 1450310
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-410c7e0886004c46b86f1c1c68aec268
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05602118

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