Water → 4-[2-(4-Methoxyphenyl)ethenyl]-N,N-bis(4-methylphenyl)aniline

HRID 1786093Notes

Reaction equation

HRID 1786093 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7]P(=O)(OCC)OCC)=[CH:5][CH:4]=1.[C:18]1([CH3:40])[CH:23]=[CH:22][C:21]([N:24]([C:33]2[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=2)[C:25]2[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=2)=[CH:20][CH:19]=1.C(O[K])(C)(C)C.O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:7]=[CH:39][C:36]2[CH:35]=[CH:34][C:33]([N:24]([C:25]3[CH:32]=[CH:31][C:28]([CH3:29])=[CH:27][CH:26]=3)[C:21]3[CH:22]=[CH:23][C:18]([CH3:40])=[CH:19][CH:20]=3)=[CH:38][CH:37]=2)=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 1707014-(Bis(p-tolyl)amino)benzaldehydeHCID 4063826Diethyl P-((4-methoxyphenyl)methyl)phosphonateHCID 178418922HCID 178418922, compound

Product 1

HCID 538532054-[2-(4-Methoxyphenyl)ethenyl]-N,N-bis(4-methylphenyl)aniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Same mol of the diethyl 4-methoxybenzylphosphonate and 4-(di-para-tolylamino)benzaldehyde were dissolved in N.N-dimethylformamide, and tert-butoxy kalium was gradually added to the solution while water-cooled and stirred. After stirred for 5 hrs at a room temperature, water was added thereto to acidize the solution and a crude product is separated out. The crude product was further column-refined with silica gel to prepare 4-methoxy-4′-(di-para-tolylamino)stilbene.

Workup

  1. temperaturecooled
  2. stirringAfter stirred for 5 hrs at a room temperature
  3. customa crude product is separated out
  4. customto prepare 4-methoxy-4′-(di-para-tolylamino)stilbene

Sources & evidence

ORD record
ord-57acaef74f0849538fd1280d535629f9
Source dataset
uspto-grants-2009_03
Patent number
US07507509B2

Reaction notes

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