Methane → (S)-5-(3,4-dihydroxy-3-methyl-1-butyl)-2,3,6-trimethylhydroquinone

HRID 1763874Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1763874
[OH:1][C@:2]([CH3:18])([CH2:16][OH:17])[CH2:3][CH2:4][C:5]1[C:6](=[O:15])[C:7]([CH3:14])=[C:8]([CH3:13])[C:9](=[O:12])[C:10]=1[CH3:11].[H][H].C>C(OCC)(=O)C.[Pd]>[OH:1][C@:2]([CH3:18])([CH2:16][OH:17])[CH2:3][CH2:4][C:5]1[C:6]([OH:15])=[C:7]([CH3:14])[C:8]([CH3:13])=[C:9]([C:10]=1[CH3:11])[OH:12]

Komponenten

6

Edukt 3

HCID 297MethaneHCID 13100536(S)-(+)-5-(3,4-dihydroxy-3-methyl-1-butyl)-2,3,6-trimethyl-p-benzoquinoneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 53635785(S)-5-(3,4-dihydroxy-3-methyl-1-butyl)-2,3,6-trimethylhydroquinoneAusbeute 100,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 0.405g (1.6mmoles) of (S)-(+)-5-(3,4-dihydroxy-3-methyl-1-butyl)-2,3,6-trimethyl-p-benzoquinone in 20 ml of ethyl acetate was stirred in an atmosphere of hydrogen, in the presence of 0.04g of 5% by weight palladium on 95% by weight charcoal until H2 uptake ceased (ca. 1hr; 38 ml H2 absorbed). The catalyst was filtered and the filtrate was concentrated giving 0.41 g of (S)-5-(3,4-dihydroxy-3-methyl-1-butyl)-2,3,6-trimethylhydroquinone as a tan solid, mp 124°-131.5°.

Aufarbeitung

  1. custom(ca. 1hr; 38 ml H2 absorbed)
  2. filtrationThe catalyst was filtered
  3. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-882cd14c17ef48f1a4869be62db102ee
Quelldatensatz
uspto-grants-1978_09
Patentnummer
US04113740

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