Methanol → Methyl 2-(4-fluorophenyl)acetate

HRID 891279Notes

Reaction equation

HRID 891279 reaction equation
S(=O)(=O)(O)O.[F:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([OH:16])=[O:15])=[CH:9][CH:8]=1.[CH3:17]O>CCOCC.C(OCC)(=O)C>[F:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 98372-(4-Fluorophenyl)acetic acid

Product 1

HCID 2733233Methyl 2-(4-fluorophenyl)acetate

Reagents, catalysts & solvents 1

HCID 21584169Diethylether ethylacetateSolvent

Procedure

A catalytic amount (0.5 mL) of concentrated sulfuric acid was added to a solution of 4-fluorophenylacetic acid (30.8 g, 0.20 mol) in 500 mL of methanol. The solution was stirred at reflux for 4 hours. The volatile materials were removed under reduced pressure to furnish a colorless oil which was dissolved in ether/ethyl acetate and washed with 2 N aqueous Na2CO3, brine, dried over MgSO4, and filtered. The filtrate was concentrated under reduced pressure to provide an oil which was dried overnight under high vacuum (yield: 33.6 g; 95%). 1H NMR (300 MHz, CDCl3) δ 3.59 (s, 2H), 3.65 (s, 3H), 7.01 (t, J=9 Hz, 2H), 7.20-7.28 (m, 2H). MS (DCI/NH3) m/z 186 (M+NH4)+.

Workup

  1. temperatureat reflux for 4 hours
  2. customThe volatile materials were removed under reduced pressure
  3. customto furnish a colorless oil which
  4. washwashed with 2 N aqueous Na2CO3, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customto provide an oil which
  9. customwas dried overnight under high vacuum (yield: 33.6 g; 95%)

Sources & evidence

ORD record
ord-b43ba8c7a9524521ad0caa20f97aecf5
Source dataset
uspto-grants-2006_02
Patent number
US07001895B2

Reaction notes

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