1,2-Dimethoxyethane → Vinyltriphenylamine
Reaction equation
[H-].[Na+].[Br-].C[PH+](C)C.[C:8]1([N:14]([C:21]2[CH:28]=[CH:27][C:24](C=O)=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CO[CH2:31][CH2:32]OC>>[CH:31]([C:22]1[CH:23]=[CH:24][CH:27]=[CH:28][C:21]=1[N:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[CH2:32]Participants
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, accusal pale yellow vinyltriphenylamine was obtained in an amount of 83.4 g (yield: 84.0%).
Workup
- temperaturethe temperature was raised to 70° C.
- customreaction for 5 hours
- customThe resulting reaction solution
- filtrationwas filtered
- extractionthe filtrate and an ether-extract of the precipitate
- washwashed with water
- customwas removed
- customto obtain a crude
- customreaction product
- customAfter recrystallized from ethanol
Sources & evidence
- ORD record
- ord-b28bcf12112c45888b219cef2808c7a2
- Source dataset
- uspto-grants-1999_03
- Patent number
- US05879847
Reaction notes
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