Water → 3-Chloro-4-methoxysalicylaldehyde

HRID 652905Notes

Reaction equation

HRID 652905 reaction equation
[Cl:1][C:2]1[C:3]([O:12]C)=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].[Al+3].[Cl-].[Cl-].[Cl-].O>ClC(Cl)C>[Cl:1][C:2]1[C:3]([OH:12])=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 133437053-Chloro-2,4-dimethoxybenzaldehyde

Product 1

HCID 133437063-Chloro-4-methoxysalicylaldehyde

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

3-chloro-2,4-dimethoxybenzaldehyde (2.75 g) is refluxed for 30 minutes in 20 ml of dichloroethane containing 1.8 g of AlCl3. The reaction mixture is then poured into H2O and extracted with CH2Cl2. Evaporation and recrystallization from isopropanol gives 3-chloro-2-hydroxy-4-methoxybenzaldehyde, mp 125° C.

Workup

  1. extractionextracted with CH2Cl2
  2. customEvaporation and recrystallization from isopropanol

Sources & evidence

ORD record
ord-56b5924c8a834416a8ea05a1b2250294
Source dataset
uspto-grants-1987_06
Patent number
US04673746

Reaction notes

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