Dichloromethane → 2-Chloro-4-hydroxy-5-methoxybenzaldehyde

HRID 253454Notes

Reaction equation

HRID 253454 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([O:10]C)[C:7]([O:12][CH3:13])=[CH:6][C:3]=1[CH:4]=[O:5].ClCCl.[Cl-].[Cl-].[Cl-].[Al+3]>O>[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[C:7]([O:12][CH3:13])=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 2793512-Chloro-4,5-dimethoxybenzaldehydeHCID 6451240Aluminum(III) Chloride

Product 1

HCID 290002-Chloro-4-hydroxy-5-methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Chloro-4,5-dimethoxy-benzaldehyde (135, 2.00 g, 0.00997 mol), dichloromethane (73.44 mL) and aluminum trichloride (2.50 g, 0.0187 mol) were combined under an atmosphere of nitrogen. The reaction was stirred at room temperature overnight. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and washed with 5% ethyl acetate in hexane to provide an off-white solid (136, 757 mg, 41%). MS (ESI) [M−H+]−=185.0, 187.0.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. washwashed with 5% ethyl acetate in hexane
  6. customto provide an off-white solid (136, 757 mg, 41%)

Sources & evidence

ORD record
ord-3c53600ed01e4328b9b0ac80bc165aa0
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

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