Sulfuric Acid → 4-Methoxycinnamate methyl ester

HRID 484560

Reaktionsgleichung

Reaktionsgleichung von HRID 484560
N(OCCCCC)=O.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14](N)=[CH:13][CH:12]=1.OS(O)(=O)=O.[C:23]([O:27][CH3:28])(=[O:26])[CH:24]=[CH2:25]>CO.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:25]=[CH:24][C:23]([O:27][CH3:28])=[O:26])=[CH:13][CH:12]=1

Komponenten

7

Edukt 4

HCID 1118Sulfuric AcidHCID 7294Methyl AcrylateHCID 7732P-AnisidineHCID 10026Pentyl nitrite

Produkt 1

HCID 928414-Methoxycinnamate methyl esterAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

117 g of amyl nitrite are added slowly to a solution, cooled to about 10° C., of 123 g of p-anisidine and 100 ml of conc. H2SO4 in 400 ml of methanol and the mixture is stirred without cooling for a further 40 minutes after addition is complete It is treated with 95 g of methyl acrylate and 112 mg of Pd(OAc)2 and heated to about 55° C. until evolution of gas has ended. After cooling, the solid is filtered off with suction, washed with water and dried at 40° C. 167 g (87%) of methyl p-methoxycinnamate are obtained, m.p. 88°-89° C., Lit 89° C.

Aufarbeitung

  1. temperaturewithout cooling for a further 40 minutes
  2. additionafter addition
  3. temperatureAfter cooling
  4. filtrationthe solid is filtered off with suction
  5. washwashed with water
  6. customdried at 40° C

Quellen und Nachweise

ORD-Eintrag
ord-01bac67072f147ca90be166e658fb667
Quelldatensatz
uspto-grants-1993_07
Patentnummer
US05231223

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