Allyl bromide → 4'-(2-Propenyloxy)-[1,1'-biphenyl]-4-carboxylic Acid Ethyl Ester

HRID 440755

Reaktionsgleichung

Reaktionsgleichung von HRID 440755
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH2:19](Br)[CH:20]=[CH2:21].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:17]([O:16][C:14]([C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:4]=[CH:3][C:2]([O:1][CH2:21][CH:20]=[CH2:19])=[CH:7][CH:6]=2)=[CH:9][CH:10]=1)=[O:15])[CH3:18]

Komponenten

5

Edukt 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 4049156Ethyl 4'-hydroxy-4-biphenylcarboxylate

Produkt 1

HCID 148479284'-(2-Propenyloxy)-[1,1'-biphenyl]-4-carboxylic Acid Ethyl EsterAusbeute 103 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of 10.0 g of 4'-hydroxy-[1,1'-biphenyl]-4-carboxylic acid, ethyl ester is dissolved in 100 ml of acetone and 8.02 g of allyl bromide added under a nitrogen atmosphere. While stirring 15.0 g of potassium carbonate is added and the reaction mixture refluxed for 16 hours. The reaction mixture is cooled to 0° C. and poured into 200 ml of ice-water and extracted with chloroform (3×150 ml). The combined extracts are washed with 1N HCl and water, dried (Na2SO4) and evaporated in vacuo to give 12.0 g of the desired product m.p. 89°-92° C. M+H=283.

Aufarbeitung

  1. additionis added
  2. temperaturethe reaction mixture refluxed for 16 hours
  3. extractionextracted with chloroform (3×150 ml)
  4. washThe combined extracts are washed with 1N HCl and water
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-83fcb0d932c442a3a9bc671167eec9cd
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05521173

Verknüpfte Notizen

Wird geladen…