Reaction #465942

Reaction equation

4-(N,N-diphenylamino)benzaldehyde

trimethylphosphonium bromide

sodium hydride

1,2-dimethoxyethane

→

vinyltriphenylamine

Yield 84.0%

Conditions

Workup

1. 1
   Temperaturethe temperature was raised to 70° C.
2. 2
   Otherreaction for 5 hours
3. 3
   OtherThe resulting reaction solution
4. 4
   Filtrationwas filtered
5. 5
   Extractionthe filtrate and an ether-extract of the precipitate
6. 6
   Washwashed with water
7. 7
   Otherwas removed
8. 8
   Otherto obtain a crude
9. 9
   Otherreaction product
10. 10
    OtherAfter recrystallized from ethanol

Procedure

Into a three-necked flask, 14.6 g of sodium hydride and 700 ml of 1,2-dimethoxyethane were placed, and 130.8 g of trimethylphosphonium bromide was added thereto with stirring at room temperature. Next, after a drop of absolute alcohol was added, the reaction was allowed to proceed at 70° C. for 4 hours. Then, 100 g of 4-(N,N-diphenylamino)benzaldehyde was added thereto, and the temperature was raised to 70° C. to carry out reaction for 5 hours. The resulting reaction solution was filtered, and the filtrate and an ether-extract of the precipitate were put together and washed with water. Then, the ether solution was dehydrated with calcium chloride, and ether was removed to obtain a crude reaction product. After recrystallized from ethanol, acicular pale yellow vinyltriphenylamine was obtained in an amount of 83.4 g (yield: 84.0%).

Source