Reacción #2025286

Ecuación de reacción

(-)-4-acetyl-4'-(2-hydroxypropyl)biphenyl

propyl iodide

→

(-)-4-acetyl-4'-(2-propoxypropyl)biphenyl

Rendimiento 30.5%

Disolventes

CHCl3

chloroform

silver

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroInto a four-necked flask provided with a stirrer
2. 2
   Filtraciónwas filtered off
3. 3
   Concentraciónthe filtrate was concentrated under a reduced pressure
4. 4
   LavadoThe resulting residue was subjected to a silica gel column chromatography (elution medium: toluene/ethyl acetate=10/1)

Procedimiento

Into a four-necked flask provided with a stirrer and a thermometer, 25.4 g of (-)-4-acetyl-4'-(2-hydroxypropyl)biphenyl (XXIII-43) [0.1 mol, [α]D20 =-11.2° (C=1, CHCl3)], 69.5 g (0.3 mol) of silver oxide and 255 g (1.5 mol) of propyl iodide were charged, and then stirred at room temperature for 15 days. Thereafter, the reaction mixture was diluted with 300 ml of chloroform, and silver salt was filtered off, and thereafter, the filtrate was concentrated under a reduced pressure. The resulting residue was subjected to a silica gel column chromatography (elution medium: toluene/ethyl acetate=10/1) to obtain 9.0 g of (-)-4-acetyl-4'-(2-propoxypropyl)biphenyl (XXII-43) [yield=30.5%, [α]D20 =-10.2° (C=1, CHCl3), m.p.=53°-55° C.] and 17.4 g of the starting material (XXIII-43) with recovery of 68.5%.

Fuente