4-Toluenesulfonyl chloride → Ethyl 2-(4-vinylphenoxy)isobutyrate

HRID 1605119Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1605119
O[CH:2]([C:4]1[CH:18]=[CH:17][C:7]([O:8][C:9]([CH3:16])([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=1)[CH3:3].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>N1C=CC=CC=1>[CH:2]([C:4]1[CH:18]=[CH:17][C:7]([O:8][C:9]([CH3:16])([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=1)=[CH2:3]

Komponenten

4

Edukt 2

HCID 73974-Toluenesulfonyl chlorideHCID 103599Ethyl 2-(4-(1-hydroxyethyl)phenoxy)isobutyrate

Produkt 1

HCID 104107Ethyl 2-(4-vinylphenoxy)isobutyrate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A mixture of 116 g. of ethyl 2-[4-(1-hydroxyethyl)phenoxy]-2-methylpropionate and 92 g. of p-toluenesulfonyl chloride in 500 ml. of pyridine was heated at reflux for three hours, kept at room temperature for about 16 hours and then heated at reflux again for six hours. The reaction mixture was poured into ice water and extracted with hexane. The hexane solution was washed successively with dilute sulfuric acid, 10% potassium bicarbonate, water and saturated sodium chloride solution, then dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was distilled at 104°-111°C. (0.03-0.08 mm.) to give60 g. of ethyl 2-(p-vinylphenoxy)-2-methylpropionate.

Aufarbeitung

  1. additionA mixture of 116 g
  2. temperatureat reflux for three hours
  3. temperatureheated
  4. temperatureat reflux again for six hours
  5. extractionextracted with hexane
  6. washThe hexane solution was washed successively with dilute sulfuric acid, 10% potassium bicarbonate, water and saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. distillationThe residue was distilled at 104°-111°C. (0.03-0.08 mm.) to give60

Quellen und Nachweise

ORD-Eintrag
ord-9d0e138a466847e68b01e9ff93c5274b
Quelldatensatz
uspto-grants-1976_04
Patentnummer
US03948973

Notizen zur Reaktion

Wird geladen…