Ethanol → Ethyl 3-chloro-5-trifluoromethoxyphenylacetate

HRID 1717470Notes

Reaction equation

HRID 1717470 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:13][C:14]([OH:16])=[O:15])[CH:5]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:7]=1.C([O-])(O)=O.[Na+].[CH3:22][CH2:23]O>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:13][C:14]([O:16][CH2:22][CH3:23])=[O:15])[CH:5]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 219046383-Chloro-5-(trifluoromethoxy)phenylacetic acid

Product 1

HCID 21904618Ethyl 3-chloro-5-trifluoromethoxyphenylacetateYield 96%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

To a solution of 3-chloro-5-trifluoromethoxyphenylactic acid (5.2 g, 20.4 mmol; see step (iii) above) in EtOH (600 mL) was added sulfuric acid (several drops). The solution was refluxed for 18 h, cooled to room temperature, neutralized with solid NaHCO3 and the EtOH removed in vacuo. The residue was diluted with EtOAc then washed with H2O (1×), aqueous NaHCO3 (1×) and brine (1×). The organics were dried (Na2SO4), filtered and concentrated in vacuo to afford the sub-title compound (5.5 g, 96%) as an oil which was used in the next step without further purification.

Workup

  1. temperatureThe solution was refluxed for 18 h
  2. customthe EtOH removed in vacuo
  3. additionThe residue was diluted with EtOAc
  4. washthen washed with H2O (1×), aqueous NaHCO3 (1×) and brine (1×)
  5. dry with materialThe organics were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cc36287251ee42a4a77e5dea4c05df77
Source dataset
uspto-grants-2010_09
Patent number
US07803954B2

Reaction notes

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