(E)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl benzoate → (E)-3-methyl-5-(2,4,5-trimethyl-3,6-dioxo-1,4-cyclohexadien-1-yl)-2-pentenyl benzoate

HRID 1195472Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1195472
[C:1]([O:9][CH2:10]/[CH:11]=[C:12](\[CH3:28])/[CH2:13][CH2:14][C:15]1[C:20]([CH3:21])=[C:19]([O:22]C)[C:18]([CH3:24])=[C:17]([CH3:25])[C:16]=1[O:26]C)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O.C(#N)C>[C:1]([O:9][CH2:10]/[CH:11]=[C:12](\[CH3:28])/[CH2:13][CH2:14][C:15]1[C:16](=[O:26])[C:17]([CH3:25])=[C:18]([CH3:24])[C:19](=[O:22])[C:20]=1[CH3:21])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 1

HCID 86745747(E)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl benzoate

Produkt 1

HCID 67900681(E)-3-methyl-5-(2,4,5-trimethyl-3,6-dioxo-1,4-cyclohexadien-1-yl)-2-pentenyl benzoateAusbeute 73,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of ceric ammonium nitrate (7.2 g; 13.1 mmol) in water (30 ml) was added dropwise while cooling with ice to a solution of (E)-5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-3-methyl-2-pentenyl benzoate (2 g; 5.2 mmol) in acetonitrile (30 ml). After completion of the addition the mixture was diluted with water and extracted with chloroform. The extracts were washed with water, dried and freed from solvent. The residue crystallizes spontaneously and 1.35 g of (E)-3-methyl-5-(2,4,5-trimethyl-3,6-dioxo-1,4-cyclohexadien-1-yl)-2-pentenyl benzoate was obtained. M.P, 74.5°-75.5° C.

Aufarbeitung

  1. additionAfter completion of the addition the mixture
  2. extractionextracted with chloroform
  3. washThe extracts were washed with water
  4. customdried
  5. customThe residue crystallizes spontaneously

Quellen und Nachweise

ORD-Eintrag
ord-673068a0194047c58e76f7f6f95cdaee
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05110955

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