Methanol → Methyl 2-(4-fluorophenyl)acetate

HRID 962483Notes

Reaction equation

HRID 962483 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>>[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

3

Reactant 2

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

Product 1

HCID 2733233Methyl 2-(4-fluorophenyl)acetate

Procedure

4-Fluorophenyl acetic acid (25 g) was dissolved in anhydrous methanol, stirred under nitrogen and cooled in an ice/methanol bath. Dry HCl gas was bubbled through the reaction for 1 hr. The methanol was removed by rotary evaporator and the residue was dispersed between aqueous sodium hydrogen carbonate and dichloromethane. The organic layer was washed with brine, dried (MgSO4) and concentrated to afford the title compound as a clear oil (24.4 g). 1H NMR (360 MHz, CDCl3) δ 3.61 (2H, s), 3.70 (3H, s), 6.97-7.06 (2H, m), 7.20-7.27 (2H, m). MS Cl+ 169 [M+H]+.

Workup

  1. temperaturecooled in an ice/methanol bath
  2. customDry HCl gas was bubbled through the reaction for 1 hr
  3. customThe methanol was removed by rotary evaporator
  4. additionthe residue was dispersed between aqueous sodium hydrogen carbonate and dichloromethane
  5. washThe organic layer was washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1252c46067de4994bfcee6542921ea25
Source dataset
uspto-grants-1998_06
Patent number
US05760018

Reaction notes

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