Dimethyl Sulfoxide → 4-Ethynyl-1,1'-biphenyl

HRID 918030

Reaktionsgleichung

Reaktionsgleichung von HRID 918030
CC(C)([O-])C.[K+].CS(C)=O.Br[CH:12]([C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:17][CH:16]=1)[CH2:13]Br>C(O)(C)(C)C>[CH:13]#[C:12][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:17][CH:16]=1

Komponenten

5

Edukt 3

HCID 679Dimethyl SulfoxideHCID 12788040HCID 12788040, VerbindungHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 344644-Ethynyl-1,1'-biphenylAusbeute 90,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

To a solution of 26 g of potassium t-butoxide in 400 ml of a 1:1 mixture (v/v) of dimethyl sulfoxide and t-butanol at 10°-15° was added with stirring a solution of 39 g of 4-(1,2-dibromoethyl)biphenyl in 400 ml of the same solvent mixture. After stirring for 20 minutes, the reaction mixture was poured into ice-water. The resulting mixture was extracted with diethyl ether. The diethyl ether then was washed successively with water, five percent aqueous sodium bicarbonate, and water, and dried over anhydrous sodium sulfate. The diethyl ether was distilled under reduced pressure and the solid residue crystallized from aqueous ethanol to give 18.5 g of crude 4-biphenylacetylene, mp 79°-81°. Two recrystallizations from hexane gave pure 4-biphenylacetylene, mp 82°-85°. The following elemental analysis was obtained:

Aufarbeitung

  1. extractionThe resulting mixture was extracted with diethyl ether
  2. washThe diethyl ether then was washed successively with water, five percent aqueous sodium bicarbonate, and water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe diethyl ether was distilled under reduced pressure
  5. customthe solid residue crystallized from aqueous ethanol

Quellen und Nachweise

ORD-Eintrag
ord-0206847ad9194784bb54ffcb6065814f
Quelldatensatz
uspto-grants-1976_07
Patentnummer
US03968251

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