Water → 3-Chloro-2,4-dimethoxybenzaldehyde

HRID 568674Notes

Reaction equation

HRID 568674 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:5]([O:6][CH3:7])[C:4]=1[Cl:11].[CH3:12][O:13]C(Cl)Cl.O>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[Cl:11][C:4]1[C:3]([O:2][CH3:1])=[C:10]([CH:9]=[CH:8][C:5]=1[O:6][CH3:7])[CH:12]=[O:13]

Participants

6

Reactant 3

HCID 962WaterHCID 21004Methane, dichloromethoxy-HCID 130157172-Chloro-1,3-dimethoxybenzene

Product 1

HCID 133437053-Chloro-2,4-dimethoxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

2-chlororesorcinol dimethyl ether (3.4 g) is dissolved in 20 ml of CH2Cl2 and TiCl4 (4.3 ml) is added. To this solution is added dichloromethyl methyl ether (2.3 g). After 30 minutes the reaction mixture is poured into H2O and extracted with ether. Drying and evaporation gives 3-chloro-2,4-dimethoxybenzaldehyde, mp 107°-108° C.

Workup

  1. extractionextracted with ether
  2. customDrying
  3. customevaporation

Sources & evidence

ORD record
ord-bb754afce9a54c8ebd5bde9bc76de249
Source dataset
uspto-grants-1988_03
Patent number
US04728662

Reaction notes

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