Methanol → Methyl (3-(trifluoromethyl)phenyl)acetate

HRID 5603

Reaktionsgleichung

Reaktionsgleichung von HRID 5603
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([CH2:9][C:10]([OH:12])=[O:11])[CH:6]=[CH:7][CH:8]=1.[CH3:15]O>CCOC(C)=O>[CH3:15][O:11][C:10](=[O:12])[CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:13])([F:14])[F:1])[CH:4]=1

Komponenten

4

Edukt 2

HCID 887MethanolHCID 676953-(Trifluoromethyl)benzeneacetic acid

Produkt 1

HCID 2734603Methyl (3-(trifluoromethyl)phenyl)acetateAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Into a solution of 3-trifluoromethylphenylacetic acid (20.0 g. 98 mmol) in MeOH (100 mL), cooled in an ice-water bath, was bubbled HCl (g) for 15 min. The mixture was allowed to warm to room temperature and was then concentrated in vacuo to furnish a clear, yellow-green liquid which was diluted with EtOAc (0.25L) and washed with saturated aqueous NaHCO3 (2×0.25L), brine (0.25L), and dried (Na2SO4). Concentration in vacuo provided the crude ester which was purified by chromatography on a column of silica gel(230-400 mesh, 600 g, 70 mm o.d., ethyl acetate-hexanes 10:90, 400 mL fractions) using the flash technique. Fractions 6-9 provided 19.08 g (89%) of methyl-3-trifluoromethylphenylacetate as a clear colorless liquid.

Aufarbeitung

  1. customwas bubbled HCl (g) for 15 min
  2. concentrationwas then concentrated in vacuo
  3. customto furnish a clear, yellow-green liquid which
  4. washwashed with saturated aqueous NaHCO3 (2×0.25L), brine (0.25L)
  5. dry with materialdried (Na2SO4)
  6. concentrationConcentration in vacuo
  7. customprovided the crude ester which
  8. customwas purified by chromatography on a column of silica gel(230-400 mesh, 600 g, 70 mm o.d., ethyl acetate-hexanes 10:90, 400 mL fractions)

Quellen und Nachweise

ORD-Eintrag
ord-1e607e457e3c44ccb98525fa715b1116
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05245046

Verknüpfte Notizen

Wird geladen…