Acetophenone → 4,4'-methylenebis{N-(alpha-methylbenzylidene)aniline}

HRID 267705

Reaction equation

HRID 267705 reaction equation
[CH2:1]([C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1)[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=O)[CH3:17]>C1(C)C=CC=CC=1>[CH2:1]([C:2]1[CH:3]=[CH:4][C:5]([N:6]=[C:1]([CH3:9])[C:2]2[CH:8]=[CH:7][CH:5]=[CH:4][CH:3]=2)=[CH:7][CH:8]=1)[C:9]1[CH:15]=[CH:14][C:12]([N:13]=[C:16]([CH3:17])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 7410AcetophenoneHCID 75774,4-Diaminodiphenylmethane

Product 1

HCID 213888954,4'-methylenebis{N-(alpha-methylbenzylidene)aniline}

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4,4'-methylene dianiline (198 g; 1 mole), acetophenone (240 g; 2 moles) and a catalytic amount of stannous chloride was refluxed in toluene (3L) for 30 hours using a Dean-Stark trap. The theoretical amount of water was removed from the system. The toluene was then removed under vacuum.

Workup

  1. customThe theoretical amount of water was removed from the system
  2. customThe toluene was then removed under vacuum

Sources & evidence

ORD record
ord-4c305abc2c81423a93ea19c9f6858e66
Source dataset
uspto-grants-1976_03
Patent number
US03944525

Linked notes

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