Water → p-n-Tetradecyloxy-4-(2-methylbutoxycarbonyl)benzylideneaniline

HRID 482818Notes

Reaction equation

HRID 482818 reaction equation
[CH3:1][CH:2]([CH2:15][CH3:16])[CH2:3][O:4][C:5]([C:7]1[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=1)=[O:6].[CH2:17]([O:31][C:32]1[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH2:17]([O:31][C:32]1[CH:38]=[CH:37][C:35]([N:36]=[CH:11][C:10]2[CH:13]=[CH:14][C:7]([C:5]([O:4][CH2:3][CH:2]([CH3:1])[CH2:15][CH3:16])=[O:6])=[CH:8][CH:9]=2)=[CH:34][CH:33]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 191002p-(n-Tetradecyloxy)phenylamineHCID 13548338p-(2-Methylbutoxycarbonyl)benzaldehyde

Product 1

HCID 13628479p-n-Tetradecyloxy-4-(2-methylbutoxycarbonyl)benzylideneaniline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

44.3 g of said p-(2-methylbutoxycarbonyl)benzaldehyde, 32 g of p-n-tetradecyloxyaniline, and 0.1 g of p-toluenesulfonic acid were dissolved in toluene. The solution was heated under reflux, and water generated in the dehydrating condensation was removed with a Dean-Stark condenser. After the reaction solution was cooled, the organic layer was washed with water, and the solvent (toluene) was distilled off in vacuum. The solid residue was recrystallized from ethanol to obtain yellow crystals.

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux
  3. customwas removed with a Dean-Stark condenser
  4. temperatureAfter the reaction solution was cooled
  5. washthe organic layer was washed with water
  6. distillationthe solvent (toluene) was distilled off in vacuum
  7. customThe solid residue was recrystallized from ethanol
  8. customto obtain yellow crystals

Sources & evidence

ORD record
ord-063c506506db4d19beb5dc80ac421b83
Source dataset
uspto-grants-1986_03
Patent number
US04576732

Reaction notes

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