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

HRID 1833318Notes

Reaction equation

HRID 1833318 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-660c0b08c70b496b97940d321a898ae3
Source dataset
uspto-grants-1978_01
Patent number
US04066609

Reaction notes

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