Water → 2-(p-Isobutylphenyl)propionic acid benzyl ester

HRID 26449

Reaktionsgleichung

Reaktionsgleichung von HRID 26449
[Na+].[CH2:2]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]([CH3:16])[C:13]([O-:15])=[O:14])=[CH:8][CH:7]=1)[CH:3]([CH3:5])[CH3:4].[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>CN(C)C=O>[CH2:17]([O:14][C:13](=[O:15])[CH:12]([C:9]1[CH:8]=[CH:7][C:6]([CH2:2][CH:3]([CH3:5])[CH3:4])=[CH:11][CH:10]=1)[CH3:16])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 7503Benzyl ChlorideHCID 5338317Ibuprofen, Sodium Salt

Produkt 1

HCID 104246622-(p-Isobutylphenyl)propionic acid benzyl esterAusbeute 86,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a mixture of 2.28 g of 2-(p-isobutylphenyl)propionic acid sodium salt in 20 ml of dimethylformamide was added 2.52 g of benzyl chloride and the whole was heated at 90° C. for 3 hours. After the reaction was complete, the solvent was removed by distillation under reduced pressure to leave a residue, to which was added water. The resulting mixture was extracted with ether and the extract was dehydrated. The ether was removed by distillation to give an oily product. Distillation of this product under reduced pressure yielded 2.57 g of 2-(p-isobutylphenyl)propionic acid benzyl ester as a colorless oil, boiling at 108°-110° C./0.1 mmHg. Analysis-Calculated for C20H24O2 : C, 81.04; H, 8.16. Found: C, 80.92; H, 8.02.

Aufarbeitung

  1. customthe solvent was removed by distillation under reduced pressure
  2. customto leave a residue
  3. extractionThe resulting mixture was extracted with ether
  4. customThe ether was removed by distillation
  5. customto give an oily product
  6. distillationDistillation of this product under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4f232384f543447b942e3eaf5c6ef308
Quelldatensatz
uspto-grants-1979_04
Patentnummer
US04150137

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