Thionyl Chloride → 2-(3,4,5-Trimethoxyphenyl)benzyl chloride

HRID 1634868Notes

Reaction equation

HRID 1634868 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=2[CH2:15]O)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].S(Cl)([Cl:23])=O>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=2[CH2:15][Cl:23])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 213388232-(3,4,5-Trimethoxyphenyl)benzyl Alcohol

Product 1

HCID 120163292-(3,4,5-Trimethoxyphenyl)benzyl chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-(3,4,5-Trimethoxyphenyl)benzyl alcohol (630 mg) was dissolved in chloroform (10 mL), and to the solution thionyl chloride (0.153 mL) was added at 0° C. After 30 minutes, the mixture was warmed to room temperature and stirred for 4 hours. The reaction mixture was washed with water and saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was then recrystallized from chloroform-hexane to obtain the title compound.

Workup

  1. washThe reaction mixture was washed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was then recrystallized from chloroform-hexane

Sources & evidence

ORD record
ord-3594760b0a684fcca052647f78d4465c
Source dataset
uspto-grants-2003_01
Patent number
US06509329B1

Reaction notes

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