Water → 2,3-Dichloro-4,5-dimethoxybenzaldehyde

HRID 1089166

Reaction equation

HRID 1089166 reaction equation
Cl[CH:2](Cl)[O:3]C.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([O:15][CH3:16])[C:8]=1[Cl:17].O>C(Cl)Cl.[Ti](Br)(Br)(Br)Br>[Cl:6][C:7]1[C:8]([Cl:17])=[C:9]([O:15][CH3:16])[C:10]([O:13][CH3:14])=[CH:11][C:12]=1[CH:2]=[O:3]

Participants

6

Reactant 3

HCID 962WaterHCID 21004Methane, dichloromethoxy-HCID 560611,2-Dichloro-3,4-dimethoxybenzene

Product 1

HCID 147486342,3-Dichloro-4,5-dimethoxybenzaldehydeYield 76.2%

Reagents, catalysts & solvents 2

HCID 123263Titanium tetrabromideCatalystHCID 6344DichloromethaneSolvent

Procedure

105.2 g of dichloromethoxymethane are added to a solution of 122.6 g of 1,2-dichloro-3,4-dimethoxybenzene in methylene chloride, and titanium tetrabromide is added dropwise to the mixture at -50° to -60° C. The mixture is stirred at room temperature for 20 hours. The reaction mixture is poured into water and the organic layer is separated. The aqueous layer is extracted with chloroform, and the extract and the above-obtained organic layer are combined. The mixture is washed with water, dried and evaporated to remove solvent. The residue is washed with n-hexane to give 106 g of 2,3-dichloro-4,5-dimethoxybenzaldehyde.

Workup

  1. additionis added dropwise to the mixture at -50° to -60° C
  2. customthe organic layer is separated
  3. extractionThe aqueous layer is extracted with chloroform
  4. extractionthe extract
  5. washThe mixture is washed with water
  6. customdried
  7. customevaporated
  8. customto remove solvent
  9. washThe residue is washed with n-hexane

Sources & evidence

ORD record
ord-ade9d4bb5d6b4a02a98c6250dc8a38bc
Source dataset
uspto-grants-1990_10
Patent number
US04965282

Linked notes

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