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Hydrochloric Acid → Methyl 2,5-dimethyl-4-trifluoromethanesulfonyloxybenzoate

HRID 2243522
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2243522
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].O[C:17]1[C:26]([CH3:27])=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[C:19]([CH3:28])[CH:18]=1.N1C=CC=CC=1.Cl>C(Cl)Cl.C(OC(=O)C)C>[CH3:28][C:19]1[CH:18]=[C:17]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])[C:26]([CH3:27])=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 22615980Methyl 4-hydroxy-2,5-dimethylbenzoate

Produkt 1

HCID 86605503Methyl 2,5-dimethyl-4-trifluoromethanesulfonyloxybenzoateAusbeute 90,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344
Dichloromethane
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Trifluoromethanesulfonic anhydride (0.27 g) was added to an ice-cooled mixture of methyl 4-hydroxy-2,5-dimethylbenzoate (0.144 g) and pyridine (0.095 g) in methylene chloride (10 mL) with stirring. The mixture was stirred at room temperature for 30 min, and poured into a mixture of ethylacetate and 2 mol/L hydrochloric acid. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=10/1) to afford the title compound (0.226 g).

Aufarbeitung

  1. temperaturecooled
  2. stirringThe mixture was stirred at room temperature for 30 min
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=10/1)

Quellen und Nachweise

ORD-Eintrag
ord-9c1685d40eb64cf4bb1da593472960fb
Quelldatensatz
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07674938B2

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