Water → Benzylidene-p-(1-methyl-heptyloxy)aniline

HRID 34255Notes

Reaction equation

HRID 34255 reaction equation
[CH:1](=[N:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].[C:18]([O-])(O)=O.[Na+].O.[C:24]1([CH3:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(O)C>[CH:1](=[N:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH:24]([CH3:30])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH3:18])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 962WaterHCID 1140TolueneHCID 115014-BenzylideneaminophenolHCID 14797Potassium HydroxideHCID 516892Sodium Bicarbonate

Product 1

HCID 21299030Benzylidene-p-(1-methyl-heptyloxy)aniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Benzylidene-p-hydroxyaniline as a known substance (m.p.: 185° C.) (140 g) was dissolved in ethanol (700 ml) containing KOH (43 g), followed by dropwise adding S(+)-2-octyl p-toluenesulfonate (218 g) at 70° C., heating the mixture under reflux for 20 hours, adding a 5% aqueous solution of NaHCO3 (50 ml), water (200 ml) and toluene (800 ml), separating the toluene layer, washing with a 2N aqueous solution of NaOH, distilling off toluene and recrystallizing from ethanol to obtain optically active benzylidene-p-(1-methyl-heptyloxy)aniline (m.p. 47.3° C.)(105 g).

Workup

  1. temperatureheating the mixture
  2. temperatureunder reflux for 20 hours
  3. customseparating the toluene layer
  4. washwashing with a 2N aqueous solution of NaOH
  5. distillationdistilling off toluene
  6. customrecrystallizing from ethanol

Sources & evidence

ORD record
ord-15de72543f8f49f09cea89a6a9d33285
Source dataset
uspto-grants-1988_08
Patent number
US04761246

Reaction notes

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