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

HRID 559494Notes

Reaction equation

HRID 559494 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-48ac39a0b9754e3286ad24ba503a59fd
Source dataset
uspto-grants-2011_11
Patent number
US08063080B2

Reaction notes

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