반응 #2025286

반응 방정식

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

propyl iodide

→

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

수율 30.5%

용매

CHCl3

chloroform

silver

반응 조건

후처리

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

실험 절차

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%.

출처