Sulfuric Acid → Methyl 3-(2-nitrophenyl)prop-2-enoate

HRID 1919552

Reaktionsgleichung

Reaktionsgleichung von HRID 1919552
[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[CH:6]=[CH:7][C:8]([OH:10])=[O:9])([O-:3])=[O:2].S(=O)(=O)(O)O.[C:20](=O)(O)[O-].[Na+]>CO>[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[CH:6]=[CH:7][C:8]([O:10][CH3:20])=[O:9])([O-:3])=[O:2]

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 928203-(2-Nitrophenyl)acrylic acidHCID 516892Sodium Bicarbonate

Produkt 1

HCID 220809Methyl 3-(2-nitrophenyl)prop-2-enoateAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 2-nitrocinnamic acid (7) (10.38 g, 53.76 mmol) dissolved in methanol (200 ml) was dropped a small amount of concentrated sulfuric acid at room temperature, and the reaction mixture was stirred at 70° C. for 12 hours. After the reaction was completed, the resulting solution was basified with a saturated aqueous solution of sodium bicarbonate to weak basicity and extracted with dichloromethane three times. Then, the organic phase was dried with anhydrous magnesium sulfate and distilled under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent: ethyl acetate:hexane=1:5) to give the target compound (11.03 g, 99%).

Aufarbeitung

  1. extractionextracted with dichloromethane three times
  2. dry with materialThen, the organic phase was dried with anhydrous magnesium sulfate
  3. distillationdistilled under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c1436bb127a94893a4c68dc8296ea40f
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08168646B2

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