Methanol → HCID 67482161, compound

HRID 854733Notes

Reaction equation

HRID 854733 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[C:12]([F:15])([F:14])[F:13].[CH3:16]O>S(=O)(=O)(O)O>[CH3:16][O:10][C:9](=[O:11])[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([C:12]([F:13])([F:14])[F:15])[CH:4]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 27375934-Fluoro-3-(trifluoromethyl)phenylacetic acid

Product 1

HCID 67482161HCID 67482161, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

A solution of (4-fluoro-3-trifluoromethyl-phenyl)-acetic acid (4.90 g, 22.06 mmol) in methanol (40 mL) was treated with concentrated sulfuric acid (7 drops). The reaction mixture was heated under reflux for 2 h. The reaction was then concentrated in vacuo. The residue was dissolved in ethyl acetate (100 mL) and washed with a saturated aqueous sodium bicarbonate solution (1×50 mL) and a saturated aqueous sodium chloride solution (1×50 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to give (4-fluoro-3-trifluoromethyl-phenyl)-acetic acid methyl ester (5.02 g, 96%) as a colorless oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 2 h
  3. concentrationThe reaction was then concentrated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate (100 mL)
  5. washwashed with a saturated aqueous sodium bicarbonate solution (1×50 mL)
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8fbe1e3ad22c444b8ad8f81a23ef06dd
Source dataset
uspto-grants-2007_08
Patent number
US07259166B2

Reaction notes

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