Water → HCID 21320435, compound

HRID 262255Notes

Reaction equation

HRID 262255 reaction equation
[O:1]([C:8]1[CH:24]=[CH:23][C:11]([N:12]=[CH:13][C:14]2[CH:19]=[CH:18][C:17]3[O:20][CH2:21][O:22][C:16]=3[CH:15]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1OC2C=CC(C=O)=CC=2O1.C1C=CC(OC2C=CC(N)=CC=2)=CC=1.O>C1C=CC=CC=1>[O:1]([C:8]1[CH:24]=[CH:23][C:11]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]3[O:20][CH2:21][O:22][C:16]=3[CH:15]=2)=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8438PiperonalHCID 8764(4-Aminophenoxy)benzeneHCID 438161854758-86-0

Product 1

HCID 21320435HCID 21320435, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The starting material used for catalytic hydrogenation, 4-phenoxy-(3,4-methylenedioxy-benzylidene)-aniline, is prepared as follows: the solution of 75 g of 3,4-methylenedioxy-benzaldehyde (piperonal) and 92.5 g of 4-aminodiphenyl ether in 500 ml of benzene is refluxed, with separation of water, for 8 hours. After the water has been completely separated, the reaction mixture is concentrated by evaporation; the crystals precipitated after cooling to about +5° C. are filtered off under suction; the crystal mass is recrystallised firstly in anhydrous benzene and subsequently in acetonitrile to thus obtain pure 4-phenoxy-(3,4-methylenedioxybenzylidene)-aniline, M.P. 89°-91° C.

Workup

  1. customis prepared
  2. customAfter the water has been completely separated
  3. concentrationthe reaction mixture is concentrated by evaporation
  4. customthe crystals precipitated
  5. temperatureafter cooling to about +5° C.
  6. filtrationare filtered off under suction
  7. customthe crystal mass is recrystallised firstly in anhydrous benzene and subsequently in acetonitrile to thus obtain pure 4-phenoxy-(3,4-methylenedioxybenzylidene)-aniline, M.P. 89°-91° C.

Sources & evidence

ORD record
ord-0e55f168d09742e0afd15b8d3447178d
Source dataset
uspto-grants-1979_05
Patent number
US04153731

Reaction notes

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