反応 #5149

反応方程式

(4-carbomethoxy)benzyltriphenylphosphonium bromide

methyl 4-formylbenzoate

sodium methoxide

toluene

→

4,4'-bis(carbomethoxy)stilbene

収率 79.3%

溶媒

methanol

methanol

反応条件

後処理

1. 1
   その他To a 2 L 3-neck round bottom flask fitted with a glass stopper, rubber septum
2. 2
   温度reflux condenser with a nitrogen inlet tube
3. 3
   workup.DISSOLUTIONAfter the starting material dissolved
4. 4
   温度The reaction vessel was heated
5. 5
   温度at reflux for 30 minutes
6. 6
   温度the reaction vessel was cooled at 0° C. for several hours
7. 7
   ろ過The resulting precipitate was filtered
8. 8
   その他dried in a vacuum oven

実験手順

To a 2 L 3-neck round bottom flask fitted with a glass stopper, rubber septum, and reflux condenser with a nitrogen inlet tube, was added 126.35 g (251 mmol) (4-carbomethoxy)benzyltriphenylphosphonium bromide, 49.45 g (302 mmol) methyl 4-formylbenzoate, and 632 mL 2:1 methanol:toluene. After the starting material dissolved, 63.2 mL (277 mmol) 25% sodium methoxide solution in methanol was added dropwise over several minutes. The reaction vessel was heated at reflux for 30 minutes. After cooling to room temperature, the reaction vessel was cooled at 0° C. for several hours. The resulting precipitate was filtered and dried in a vacuum oven to afford 59.0 g (79%) 4,4'-bis(carbomethoxy)stilbene as a 7:3 mixture of cis:trans isomers.

出典