Acetic Anhydride → Acetyl ferulate

HRID 1253248

Reaktionsgleichung

Reaktionsgleichung von HRID 1253248
C[C@@H]([C@@H]1[C@@]2(C)CC[C@@]34C[C@]53C[CH2:24][C@H:25]([O:29][C:30](/[CH:32]=[CH:33]/[C:34]3[CH:35]=[CH:36][C:37]([OH:42])=[C:38]([O:40][CH3:41])[CH:39]=3)=[O:31])C(C)(C)[C@@H]5CC[C@H]4[C@]2(C)CC1)CCC=C(C)C.C(OC(=O)C)(=[O:47])C>N1C=CC=CC=1>[C:30]([O:29][C:25](=[O:47])[CH3:24])(=[O:31])/[CH:32]=[CH:33]/[C:34]1[CH:35]=[CH:36][C:37]([OH:42])=[C:38]([O:40][CH3:41])[CH:39]=1

Komponenten

4

Edukt 2

HCID 7918Acetic AnhydrideHCID 5282164Gamma-Oryzanol

Produkt 1

HCID 20137027Acetyl ferulate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Commercial available γ-oryzanol (100 g, 24-methylenecycloartanol content 45%) was acetylated with acetic anhydride in pyridine. This acetylated γ-oryzanol was recrystallized repeatedly from chloroform-ethyl acetate-ethanol (4:3:2, V/V), giving acetyl ferulate (18 g) of 24-methylenecycloartanol content 95%. This acetyl ferulate was completely saponified in the solution of 2N NaOH-ethanol, then the obtained alcohol was converted into the benzoate. This benzoate was recrystallized repeatedly, and completely saponified to give 24-methylenecycloartanol (5 g). A portion (2 g, 0.0045 mole) thereof wa converted into 24-methylenecycloartanol-4-acetoxy-3-methoxycinnamate according to following the procedure of Example 65. This ester was then deacetylated according to following the procedure of Example 100-2, giving 24-methylenecycloartanol-4-hydroxy-3-methoxycinnamate (2.58 g), in a 90% yield. m.p. 166°-167° C.

Aufarbeitung

  1. customThis acetylated γ-oryzanol was recrystallized repeatedly from chloroform-ethyl acetate-ethanol (4:3:2, V/V)

Quellen und Nachweise

ORD-Eintrag
ord-cc856f7405274468858e03e11bf88e89
Quelldatensatz
uspto-grants-1988_05
Patentnummer
US04748161

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