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

HRID 494475Notes

Reaction equation

HRID 494475 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>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:13])=[O:10])=[CH:6][CH:7]=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-58bf971b7d4d4313a07069a51f0e281a
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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