反応 #2025286

反応方程式

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

propyl iodide

→

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

収率 30.5%

溶媒

CHCl3

chloroform

silver

反応条件

後処理

1. 1
   その他Into a four-necked flask provided with a stirrer
2. 2
   ろ過was filtered off
3. 3
   濃縮the filtrate was concentrated under a reduced pressure
4. 4
   洗浄The resulting residue was subjected to a silica gel column chromatography (elution medium: toluene/ethyl acetate=10/1)

実験手順

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%.

出典