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

HRID 1730627Notes

Reaction equation

HRID 1730627 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'-methylenedianiline (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-8805904a13f44ad3a72ac8db705ddfff
Source dataset
uspto-grants-1976_11
Patent number
US03993630

Reaction notes

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