Ammonium cerium-nitrate → (S)-(+)-5-(3,4-dihydroxy-3-methyl-1-butyl)-2,3,6-trimethyl-p-benzoquinone

HRID 262057Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 262057
[N+]([O-])([O-])=[O:2].[NH4+].[Ce].CO[C:9]1([CH3:29])[C:14]([CH3:15])=[C:13]([O:16]C)[C:12]([CH3:18])=[C:11]([CH2:19][CH2:20][C@@:21]2([CH3:28])[CH2:25][O:24]C(C)(C)[O:22]2)[CH2:10]1>O.C(#N)C>[OH:22][C@:21]([CH3:28])([CH2:25][OH:24])[CH2:20][CH2:19][C:11]1[C:10](=[O:2])[C:9]([CH3:29])=[C:14]([CH3:15])[C:13](=[O:16])[C:12]=1[CH3:18]

Komponenten

5

Edukt 2

HCID 57418452Ammonium cerium-nitrateHCID 70593036(S)-4-(3,5-dimethoxy-3,4,6-trimethyl-phenylethyl)-2,2,4-trimethyl-1,3-dioxolan

Produkt 1

HCID 13100536(S)-(+)-5-(3,4-dihydroxy-3-methyl-1-butyl)-2,3,6-trimethyl-p-benzoquinoneAusbeute 41,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

While stirring for 2 minutes at room temperature, 2.01 g of cerium ammonium nitrate in 7.5 ml of water were added dropwise to a solution of 550 mg of (S)-4-(3,5-dimethoxy-3,4,6-trimethyl-phenylethyl)-2,2,4-trimethyl-1,3-dioxolan in 7.5 ml of acetonitrile. After 2 minutes of additional stirring, the reaction mixture was extracted three times with 20 ml of chloroform each time. The combined organic extracts were dried over sodium sulfate, whereafter the solvent was removed. After chromatography of the obtained residue on silica gel with benzene/ethyl acetate (2:1 parts by volume) and ethyl acetate, there were obtained 266 mg of (S)-(+)-2,3,6-trimethyl-5-(2,2,4-trimethyl-1,3-dioxolan-4-ethyl)-p-benzoquinone and 177 mg of (S)-(+)-5-(3,4-dihydroxy-3-methyl-1-butyl)-2,3,6-trimethyl-p-benzoquinone in the form of yellow needles with a melting point of 111°-112°.

Aufarbeitung

  1. waitAfter 2 minutes of additional stirring
  2. extractionthe reaction mixture was extracted three times with 20 ml of chloroform each time
  3. dry with materialThe combined organic extracts were dried over sodium sulfate, whereafter the solvent
  4. customwas removed

Quellen und Nachweise

ORD-Eintrag
ord-cda46522b62f43ce85fa6f88c66430e4
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04153614

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