Thionyl Chloride → 4-(2-Chloroethyl)-1,2-dimethoxybenzene

HRID 1928541Notes

Reaction equation

HRID 1928541 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12]O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].S(Cl)([Cl:16])=O>C(Cl)(Cl)Cl>[Cl:16][CH2:12][CH2:11][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 819113,4-Dimethoxyphenethyl alcohol

Product 1

HCID 30153594-(2-Chloroethyl)-1,2-dimethoxybenzene

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The reaction mixture of 2-(3,4-dimethoxyphenyl)ethanol (6.0 g, 32.8 mmol) and thionyl chloride (19 g, 164 mmol) in chloroform (20 mL) was stirred at reflux for 4 h, concentrated, and partitioned between water and ethyl acetate. The organic layer was washed with NaHCO3 and brine, dried over anhydrous sodium sulfate, and concentrated to afford 4-(2-chloroethyl)-1,2-dimethoxybenzene (K) quantitatively (6.6 g).

Workup

  1. temperatureat reflux for 4 h
  2. concentrationconcentrated
  3. custompartitioned between water and ethyl acetate
  4. washThe organic layer was washed with NaHCO3 and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1c65b33fbc8849258d40d3a151ab7f11
Source dataset
uspto-grants-2012_05
Patent number
US08183374B2

Reaction notes

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