Water → Methyl 4-cyano-3-methoxybenzoate

HRID 1009916Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1009916
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[O:13][CH3:14])=O.Cl.[NH2:16]O.O.C(=O)([O-])O.[Na+]>C(O)=O>[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[O:13][CH3:14])#[N:16]

Komponenten

6

Edukt 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 10631650Methyl 4-formyl-3-methoxybenzoate

Produkt 1

HCID 22464400Methyl 4-cyano-3-methoxybenzoateAusbeute 91,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 284Formic AcidLösungsmittel

Versuchsvorschrift

To a solution (20 ml) of methyl 4-formyl-3-methoxybenzoate (870 mg, 4.48 mmol) in formic acid was added hydroxylamine hydrochloride (405 mg, 5.82 mmol), and the mixture was stirred at room temperature for 1 hr. The temperature was raised to 50° C., and the mixture was further stirred for 24 hrs. Water was added to the reaction mixture, the mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was dried over anhydrous MgSO4, and the solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with hexane-ethyl acetate (1:0-7:3, v/v) to give the title compound (780 mg, 91%) as a colorless oil.

Aufarbeitung

  1. temperatureThe temperature was raised to 50° C.
  2. stirringthe mixture was further stirred for 24 hrs
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous MgSO4
  5. customthe solvent was evaporated under reduced pressure
  6. washeluted with hexane-ethyl acetate (1:0-7:3

Quellen und Nachweise

ORD-Eintrag
ord-ff9c63aae68744f5abf2f6c420d9dd2c
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973163B2

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