Methanol → Methyl 2-(4-fluorophenyl)acetate

HRID 440384

Reaction equation

HRID 440384 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH3:12]O>S(=O)(=O)(O)O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 98372-(4-Fluorophenyl)acetic acid

Product 1

HCID 2733233Methyl 2-(4-fluorophenyl)acetate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
50 °C

Procedure

Combine 4-fluorophenylacetic acid (10.6 g, 68.8 mmol) and anhydrous methanol (100 mL). Add concentrated sulfuric acid (3 drops). Heat at 50° C. After 12 hours, cool to ambient temperature and evaporate most of the solvent in vacuo. Dilute the evaporated reaction mixture with ether, extract with aqueous saturated sodium bicarbonate solution and brine. Dry over MgSO4 filter and allow to stand until a solid forms. Collect the solid by filtration to give methyl 4-fluorophenylacetate which may be used without further purification.

Workup

  1. temperaturecool to ambient temperature
  2. customevaporate most of the solvent in vacuo
  3. additionDilute
  4. customthe evaporated reaction mixture with ether
  5. extractionextract with aqueous saturated sodium bicarbonate solution and brine
  6. dry with materialDry over MgSO4
  7. filtrationfilter
  8. customCollect the solid
  9. filtrationby filtration

Sources & evidence

ORD record
ord-e8e4633672dc4bd5998555ecc3cc0e41
Source dataset
uspto-grants-1996_05
Patent number
US05519048

Linked notes

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