Chlorotrimethylsilane → Methyl 2-(3,4-dichlorophenyl)acetate

HRID 1434674Notes

Reaction equation

HRID 1434674 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:13][Si](Cl)(C)C>CO>[CH3:13][O:11][C:10](=[O:12])[CH2:9][C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 798743,4-Dichlorophenylacetic acid

Product 1

HCID 1268257Methyl 2-(3,4-dichlorophenyl)acetateYield 99.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (3,4-dichloro-phenyl)-acetic acid (90.5 mmol) in methanol (200 mL) was added trimethylsilylchloride (181 mmol) and the mixture was stirred overnight before it was concentrated. The residue was diluted with ether (200 mL) and the solution was washed with 1 N NaOH, brine, dried over MgSO4, and concentrated in vacuo to give (3,4-dichloro-phenyl)-acetic acid methyl ester (90 mmol) as a colorless liquid.

Workup

  1. concentrationwas concentrated
  2. additionThe residue was diluted with ether (200 mL)
  3. washthe solution was washed with 1 N NaOH, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-32d7ef95befe4784835255dd181cf7cd
Source dataset
uspto-grants-2009_11
Patent number
US07615569B2

Reaction notes

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