Hydrochloric Acid → 4-(2-Phenylpropan-2-yl)aniline

HRID 1903589Notes

Reaction equation

HRID 1903589 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[CH2:11]>[Cl-].[Zn+2].[Cl-]>[C:10]([C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:11])[CH3:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 7407Alpha-Methylstyrene

Product 1

HCID 2348744-(2-Phenylpropan-2-yl)anilineYield 78%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

18.6 Parts of aniline, 20.4 parts of 36% w/w hydrochloric acid containing 13.6 parts of zinc chloride are stirred and refluxed for 24 hours with 23.6 parts of α-methylstyrene. The work-up follows Example 3 and gives on distillation 32.9 parts of 4-cumylaniline mb4 175°-80° C. (78% yield based on a 93% purity by G.L.C.).

Sources & evidence

ORD record
ord-7b16dcf794b84a99b98182202059afda
Source dataset
uspto-grants-1984_03
Patent number
US04436936

Reaction notes

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