Sulfuric Acid → Apogossypol

HRID 1666029Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1666029
[CH3:1][C:2]1[C:24]([C:25]2[C:26]([CH3:52])=[CH:27][C:28]3[C:38]([CH:39]([CH3:41])[CH3:40])=[C:37]([O:42]C(C)=O)[C:36]([O:46]C(C)=O)=[C:35](C=O)[C:29]=3[C:30]=2[O:31]C(C)=O)=[C:23]([O:53]C(C)=O)[C:5]2=[C:6](C=O)[C:7]([O:17]C(C)=O)=[C:8]([O:13]C(C)=O)[C:9]([CH:10]([CH3:12])[CH3:11])=[C:4]2[CH:3]=1.OS(O)(=O)=O>[OH-].[Na+]>[CH3:52][C:26]1[C:25]([C:24]2[C:2]([CH3:1])=[CH:3][C:4]3[C:9]([CH:10]([CH3:11])[CH3:12])=[C:8]([OH:13])[C:7]([OH:17])=[CH:6][C:5]=3[C:23]=2[OH:53])=[C:30]([OH:31])[C:29]2=[CH:35][C:36]([OH:46])=[C:37]([OH:42])[C:38]([CH:39]([CH3:40])[CH3:41])=[C:28]2[CH:27]=1

Komponenten

4

Edukt 2

HCID 1118Sulfuric AcidHCID 35450Gossypol hexaacetate

Produkt 1

HCID 454878ApogossypolAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

More specifically, the gossypol acetic acid 1 (5 g, 8.65 mmol) in 50 ml of 40% NaOH was heated under nitrogen at 90° C. for 3.5 hours in the dark. The reaction mixture was cooled and poured slowly onto ice (300 ml) and concentrated H2SO4 (35 ml) mixture to form white precipitation. The precipitation was filtered, washed with water and dried to afford apogossypol (3.8 g, 95%) as a white solid. 1H NMR (CDCl3 δ 7.61 (s, 2H), 7.50 (s, 2H), 5.93 (s, 2H), 5.27 (s, 2H), 5.13 (s, 2H), 3.88 (m, 2H), 2.12 (s, 6H), 1.55 (d, J=5.5 Hz, 12H).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. customto form white
  3. customprecipitation
  4. customThe precipitation
  5. filtrationwas filtered
  6. washwashed with water
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-be0e14856da841418d83d3860b5071ef
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08039668B2

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