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Methyl 10-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)-10-oxodecanoate → Methyl 10-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)decanoate

HRID 1679846
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1679846
[OH:1][C:2]1[C:21]([O:22][CH3:23])=[C:20]([O:24][CH3:25])[CH:19]=[C:18]([CH3:26])[C:3]=1[C:4]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=O.[H][H]>C(O)(=O)C.[Pd]>[OH:1][C:2]1[C:21]([O:22][CH3:23])=[C:20]([O:24][CH3:25])[CH:19]=[C:18]([CH3:26])[C:3]=1[CH2:4][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15]
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Komponenten

5

Edukt 2

HCID 12906141Methyl 10-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)-10-oxodecanoateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 12824095Methyl 10-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)decanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A solution of methyl 9-(2'-hydroxy-3',4'-dimethoxy-6'-methylbenzoyl)nonanoate (formula II-1 wherein R=H3CO, X=H, Y=OH, n=8, in the form of methyl ester) (0.12 part) in acetic acid (17 volume parts) was shaken with 5% palladium-on-carbon in a current of hydrogen gas at 50°-60° C. The catalyst was removed by filtration and the acetic acid was distilled off under reduced pressure. The residue was subjected to column chromatography on silicic acid (6 parts) and elution was carried out with chloroform. The procedure provided methyl 10-(2'-hydroxy-3',4'-dimethoxy-6'-methylphenyl)decanoate (formula II-2 wherein R=H3CO, X=H, Y=OH, n=8, in the form of methyl ester) (0.09 part) as a colorless oil.

Aufarbeitung

  1. customThe catalyst was removed by filtration
  2. distillationthe acetic acid was distilled off under reduced pressure
  3. washThe residue was subjected to column chromatography on silicic acid (6 parts) and elution

Quellen und Nachweise

ORD-Eintrag
ord-459a56b9a9fe490bae4f71c6c9899552
Quelldatensatz
uspto-grants-1981_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04271083

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