Methanol → Methyl 2-(3-fluoro-4-methoxyphenyl)acetate

HRID 1877919Notes

Reaction equation

HRID 1877919 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:10][C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].OS(O)(=O)=O.[CH3:19]O>>[CH3:19][O:12][C:11](=[O:13])[CH2:10][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([F:1])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 521176(3-Fluoro-4-methoxyphenyl)acetic acid

Product 1

HCID 14897830Methyl 2-(3-fluoro-4-methoxyphenyl)acetate

Procedure

(3-Fluoro-4-methoxyphenyl)acetic acid (5.0 g, 27.1 mmol) is dissolved in MeOH (100 mL). To it is added concentrated H2SO4 (5 mL) and the solution is warmed to reflux for 2 h. At that point, the solution is evaporated to dryness and taken up in EtOAc. The solution is washed with saturated aqueous NaHCO3, dried (Na2SO4) and evaporated to give (3-fluoro-4-methoxyphenyl)acetic acid methyl ester (cas# 588-14-7) as a yellow oil. MS (ESI) m/z 199.3 (M+H).

Workup

  1. temperaturethe solution is warmed
  2. temperatureto reflux for 2 h
  3. customAt that point, the solution is evaporated to dryness
  4. washThe solution is washed with saturated aqueous NaHCO3
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-ed662bfcabec4e81884a9e35f704e550
Source dataset
uspto-grants-2012_11
Patent number
US08314097B2

Reaction notes

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