Toluene → N-(4-butoxybenzylidene)aniline

HRID 1655111Notes

Reaction equation

HRID 1655111 reaction equation
[CH2:1]([O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1(C)C=CC=CC=1>C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[O:5]([C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[N:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:8][CH:7]=1)[CH2:1][CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 1140TolueneHCID 6115AnilineHCID 798134-Butoxybenzaldehyde

Product 1

HCID 20077676N-(4-butoxybenzylidene)anilineYield 77%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 962WaterSolvent

Procedure

A mixture of 7.2 g (0.040 mol) of 4-butoxybenzaldehyde, 4.0 g (0.044 mol) of aniline, 0.10 g of p-toluenesulfonic acid, and 75 mL of toluene was heated at reflux for 16 hr, with continuous azeotropic separation of the water evolved. Upon cooling, the contents of the flask were chromatographed on silica gel using dichloromethane as the eluent to give 7.8 g (77%) of N-(4-butoxylbenzylidene)aniline as a viscous oil. Crystallization from heptane afforded an analytical sample of a white solid.

Workup

  1. temperaturewas heated
  2. temperatureUpon cooling
  3. customthe contents of the flask were chromatographed on silica gel

Sources & evidence

ORD record
ord-78c9c483eeb6402cacc849c2c91e5a05
Source dataset
uspto-grants-1995_04
Patent number
US05410630

Reaction notes

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