Aluminum(III) Chloride → 2,3-Dichloro-4-hydroxy-N-n-butylaniline

HRID 1761667

Reaction equation

HRID 1761667 reaction equation
[Cl:1][C:2]1[C:12]([Cl:13])=[C:11]([O:14]C)[CH:10]=[CH:9][C:3]=1[NH:4][CH2:5][CH2:6][CH2:7][CH3:8].[Cl-].[Al+3].[Cl-].[Cl-]>ClC(Cl)C(Cl)Cl>[Cl:1][C:2]1[C:12]([Cl:13])=[C:11]([OH:14])[CH:10]=[CH:9][C:3]=1[NH:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 136884512,3-Dichloro-4-methoxy-N-n-butylaniline

Product 1

HCID 198144102,3-Dichloro-4-hydroxy-N-n-butylaniline

Reagents, catalysts & solvents 1

HCID 65911,1,2,2-TetrachloroethaneSolvent

Procedure

To a stirred solution of 2,3-dichloro-4-methoxy-N-n-butylaniline (8.5 g) in 1,1,2,2-tetrachloroethane (80 ml) is added anhydrous aluminium chloride (8.5 g), and the mixture is refluxed for about 40 hours. The resulting mixture is poured into ice/water (about 500 ml), and the precipitated material is extracted twice with methylene chloride. The combined extracts are dried and evaporated in vacuo to give the title compound as a heavy oil.

Workup

  1. temperaturethe mixture is refluxed for about 40 hours
  2. extractionthe precipitated material is extracted twice with methylene chloride
  3. customThe combined extracts are dried
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-8388fbe10957459ba1e0699610d265f6
Source dataset
uspto-grants-1989_05
Patent number
US04826987

Linked notes

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