Hydrochloric Acid → Methyl 2-(4-fluorophenyl)acetate

HRID 2224796Notes

Reaction equation

HRID 2224796 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.Cl.[CH3:13]O>O1CCOCC1>[CH3:13][O:10][C:9](=[O:11])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 98372-(4-Fluorophenyl)acetic acid

Product 1

HCID 2733233Methyl 2-(4-fluorophenyl)acetateYield 81%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-(4-fluorophenyl)acetic acid (15.4 g, 0.1 mol) in methanol (600 mL) was treated with a solution of hydrogen chloride in dioxane (4 N, 100 mL) followed by warming at reflux for 18 h. The solution was cooled and concentrated in vacuo. The residue was distilled under reduced pressure (55-58° C./0.5 mm Hg) to afford the title compound as colorless oil (13.6 g, 81%). 1H NMR (300 MHz, CDCl3): δ 3.60 (s, 2 H) 3.70 (s, 3 H) 7.02 (m, 2 H) 7.24 (m, 2 H).

Workup

  1. temperatureby warming
  2. temperatureat reflux for 18 h
  3. temperatureThe solution was cooled
  4. concentrationconcentrated in vacuo
  5. distillationThe residue was distilled under reduced pressure (55-58° C./0.5 mm Hg)

Sources & evidence

ORD record
ord-c29362304852408d8c643965e5de43b6
Source dataset
uspto-grants-2008_05
Patent number
US07378414B2

Reaction notes

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