Sodium hydride → 4-[N,N-bis(3,4-dimethylphenyl)amino]styrene
Reaction equation
[H-].[Na+].[Br-].[CH3:4][PH+](C)C.[CH3:8][C:9]1[CH:10]=[C:11]([N:16]([C:25]2[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=2)[C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([CH3:24])[CH:18]=2)[CH:12]=[CH:13][C:14]=1[CH3:15]>COCCOC>[CH3:8][C:9]1[CH:10]=[C:11]([N:16]([C:25]2[CH:32]=[CH:31][C:28]([CH:29]=[CH2:4])=[CH:27][CH:26]=2)[C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([CH3:24])[CH:18]=2)[CH:12]=[CH:13][C:14]=1[CH3:15]Participants
Procedure
Into a three-necked flask, 12.1 g of sodium hydride and 580 ml of 1,2-dimethoxyethane were placed, and 108.5 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, 100.0 g of 4-[N,N-bis(3,4-dimethylphenyl)amino]benzaldehyde was added to the reaction mixture, to carry out reaction at 70° C. for 5 hours, followed by filtration to collect a cake. The cake was extracted with ether and the extract was put together with the filtrate and washed with water. Then, the ether solution was dehydrated with calcium chloride, and thereafter the ether was removed to obtain a crude product. After twice recrystallized from ethanol, accusal 4-[N,N-bis(3,4-dimethylphenyl)amino]styrene was obtained in an amount of 84.5 g (yield: 85.0%).
Workup
- customreaction at 70° C. for 5 hours
- filtrationfollowed by filtration
- customto collect a cake
- extractionThe cake was extracted with ether
- washwashed with water
- customthe ether was removed
- customto obtain a crude product
- customAfter twice recrystallized from ethanol
Sources & evidence
- ORD record
- ord-c04c807abc8843a291bc094b6cbb9585
- Source dataset
- uspto-grants-1999_03
- Patent number
- US05879847
Reaction notes
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