Thionyl Chloride → 2-(2-Chloroethoxy)-1,3-dimethoxybenzene

HRID 868506Notes

Reaction equation

HRID 868506 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[C:4]=1[O:5][CH:6](O)[CH3:7].S(Cl)([Cl:17])=O>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[C:4]=1[O:5][CH2:6][CH2:7][Cl:17]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 14886366HCID 14886366, compound

Product 1

HCID 133059082-(2-Chloroethoxy)-1,3-dimethoxybenzene

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 7.77 g of 2,6-dimethoxyphenoxyethanol in 30 ml of pyridine was cooled and 4.7 g of thionylchloride was added with stirring. After 20 minutes, stirring, the reaction mixture was heated on the steam bath for 2 hours. After cooling, the reaction mixture was evaporated in reduced pressure. The residue was extracted with CHCl3, purified with silicagel chromatography (eluent: EtOAc) 1.82 g of objective compound was obtained.

Workup

  1. stirringstirring
  2. temperaturethe reaction mixture was heated on the steam bath for 2 hours
  3. temperatureAfter cooling
  4. customthe reaction mixture was evaporated in reduced pressure
  5. extractionThe residue was extracted with CHCl3
  6. custompurified with silicagel chromatography (eluent: EtOAc) 1.82 g of objective compound
  7. customwas obtained

Sources & evidence

ORD record
ord-607a922964134f7aa0ee55f90dc64397
Source dataset
uspto-grants-1988_10
Patent number
US04780462

Reaction notes

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