Methanol → Methyl 2-[3,5-bis(trifluoromethyl)phenyl]acetate

HRID 2212989Notes

Reaction equation

HRID 2212989 reaction equation
S(=O)(=O)(O)O.[F:6][C:7]([F:23])([F:22])[C:8]1[CH:9]=[C:10]([CH2:18][C:19]([OH:21])=[O:20])[CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=1.[CH3:24]O>>[F:6][C:7]([F:22])([F:23])[C:8]1[CH:9]=[C:10]([CH2:18][C:19]([O:21][CH3:24])=[O:20])[CH:11]=[C:12]([C:14]([F:16])([F:17])[F:15])[CH:13]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 1235873,5-Bis(trifluoromethyl)phenylacetic acid

Product 1

HCID 10401718Methyl 2-[3,5-bis(trifluoromethyl)phenyl]acetateYield 93%

Procedure

Sulfuric acid (conc., 1 mL) was added to a solution of 3,5-bis(trifluoromethyl)benzeneacetic acid (50.0 g, 0.18 mol) in methanol (400 mL) and the mixture was stirred at room temperature for 1 week. The solvent was evaporated and ethyl acetate (100 mL) and aqueous sodium hydrogen carbonate (saturated, 600 mL) were added. The layers were separated and the aqueous layer was extracted with ethyl acetate (2×300 mL). The combined organic fractions were washed with brine, dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound (49.0 g, 93%). 1H NMR (400 MHz, CDCl3) δ 7.80 (1H, s), 7.75 (2H, s), 3.77 (2H, s), and 3.75 (3H, s).

Workup

  1. customThe solvent was evaporated
  2. additionethyl acetate (100 mL) and aqueous sodium hydrogen carbonate (saturated, 600 mL) were added
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (2×300 mL)
  5. washThe combined organic fractions were washed with brine
  6. dry with materialdried (MgSO4)
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6f82d05f87f24112831b54cfff6329b8
Source dataset
uspto-grants-2006_09
Patent number
US07105507B2

Reaction notes

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