反应 #2320129

反应方程式

paraformaldehyde

paraformaldehyde

N-methylanilinium trifluoroacetate

diethyl ether

α-tetralone

→

2-methylene-3,4-dihydronaphthalen-1-one

收率 92.4%

溶剂

THF

反应条件

后处理

1. 1
   温度The solution was heated
2. 2
   温度at reflux under nitrogen
3. 3
   workup.DISSOLUTIONdissolved
4. 4
   温度After cooling
5. 5
   其他The solvent was separated from the reaction mixture
6. 6
   洗涤washed with 500 mL of saturated sodium bicarbonate
7. 7
   workup.ADDITIONAdditional diethyl ether was added to the reaction mixture
8. 8
   其他separated
9. 9
   萃取to back extract the aqueous sodium bicarbonate layer
10. 10
    干燥The combined organic layers were dried over magnesium sulfate
11. 11
    浓缩the solution was then concentrated to a volume of approximately 300 mL
12. 12
    过滤filtered through Celite
13. 13
    其他Complete evaporation of the ether

实验过程

To a suspension of paraformaldehyde (46.2 g, 1.54 mol) and N-methylanilinium trifluoroacetate (TAMA, 46.2 g, 1.54 mol) in 340 mL of dry THF was added α-tetralone (50 g, 0.342 mol). The solution was heated at reflux under nitrogen with stirring for 4 h, during which time the paraformaldehyde dissolved. After cooling, diethyl ether (700 mL) was added to the reaction mixture. The solvent was separated from the reaction mixture and washed with 500 mL of saturated sodium bicarbonate. Additional diethyl ether was added to the reaction mixture, separated and used to back extract the aqueous sodium bicarbonate layer. The combined organic layers were dried over magnesium sulfate, and the solution was then concentrated to a volume of approximately 300 mL and filtered through Celite. Complete evaporation of the ether yielded 50 g (90%) of crude 2-methylene-3,4-dihydronaphthalen-1-one, which was used immediately for the next reaction to prevent polymerization of the product.

来源