Reaktion #171500

Reaktionsgleichung

(8-Bromo-octyl)-benzene

2,4-lutidine

→

product

Ausbeute 70.0%

2,4-dimethyl-1-(8-phenyl-octyl)-pyridinium bromide

Ausbeute 70.0%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe solution refluxed for 24 hours
2. 2
   SonstigeThe acetonitrile was removed in a vacuum
3. 3
   Sonstigethe resulting residue was partitioned between ether and water
4. 4
   WaschenThe aqueous layer was washed extensively with ether until no 2,4-lutidine
5. 5
   workup.WAITwas left in the aqueous layer
6. 6
   ExtraktionThe resulting aqueous solution of the product was extracted with chloroform
7. 7
   SonstigeThe chloroform was removed

Vorschrift

(8-Bromo-octyl)-benzene (1 mmol) was added to a solution of 2,4-lutidine (3 mmol) in acetonitrile, and the solution refluxed for 24 hours. The acetonitrile was removed in a vacuum and the resulting residue was partitioned between ether and water. The aqueous layer was washed extensively with ether until no 2,4-lutidine was left in the aqueous layer. The resulting aqueous solution of the product was extracted with chloroform. The chloroform was removed to afford the product (70%). 1HNMR (300 MHz, CDCl3, ppm), 9.50 (d, 1H), 7.70 (d, 1H), 7.60 (s, 1H), 7.10-7.30 (dd, 1H), 4.78 (t, 2H), 2.84 (s, 3H), 2.54-2.60 (m, 5H), 1.80-1.92 (m, 2H), 1.50-1.60 (br, 2H), 1.20-1.45 (br, 6H).

Quelle