Water → HCID 12507348, Verbindung

HRID 728530Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 728530
O.C(O)[C@H]1O[C@H](O[C@]2(CO)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O.[Cl:25][C:26]1([Cl:35])[CH:33]2[CH:28]([CH2:29][CH2:30][CH:31]=[CH:32]2)[C:27]1=[O:34]>C(O)C>[Cl:25][C:26]1([Cl:35])[C@@H:33]2[C@@H:28]([CH2:29][CH2:30][CH:31]=[CH:32]2)[C:27]1=[O:34].[Cl:25][C:26]1([Cl:35])[C@H:33]2[C@H:28]([CH2:29][CH2:30][CH:31]=[CH:32]2)[C@@H:27]1[OH:34]

Komponenten

6

Edukt 3

HCID 962WaterHCID 5988Sucrose2×HCID 125073478,8-Dichlorobicyclo[4.2.0]oct-2-en-7-one

Produkt 2

HCID 12507348HCID 12507348, VerbindungHCID 14127271HCID 14127271, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
32 °C

Versuchsvorschrift

A mixture of 3 liters of water, 150 g of an active Bakers Yeast, 15 g of edible yeast and 10 g of sucrose were stirred at 32° C. A solution of 24 g of 8,8-dichloro-bicyclo[4.2.0]oct-2-en-7-one in 170 ml of ethanol was added dropwise over a 15 minute period, followed by a further 5 g of sucrose. After stirring for 45 minutes the reaction mixture was centrifuged to remove the yeast, which was washed with acetone and the washings combined with the aqueous product from the centrifuge. The combined product was washed several times with ethyl acetate, the organic washings combined filtered and the solvent removed from the filtrate under reduced pressure. The residue was chromatographed on silica gel, eluting with 5% acetone in hexane, initially and gradually increasing the proportion of acetone to 100%, giving 4.0 g of (1S,6R)-8,8-dichlorobicyclo[4.2.0]oct-2-en-7-one (4) as a liquid, [α]D =-78.7° (C=0.8, CHCl3), and 8.8 g of crude (1R,6S,7S)-8,8-dichlorobicyclo[4.2.0]oct-2-en-7-ol (5), which was recrystallized from hexane to give 6.4 g of pure (5), m.p.=86°-7° C., [α]D =-217.1° (C=0.6, CHCl3).

Aufarbeitung

  1. stirringAfter stirring for 45 minutes the reaction mixture
  2. customto remove the yeast, which
  3. washwas washed with acetone
  4. washThe combined product was washed several times with ethyl acetate
  5. filtrationthe organic washings combined filtered
  6. customthe solvent removed from the filtrate under reduced pressure
  7. customThe residue was chromatographed on silica gel
  8. washeluting with 5% acetone in hexane
  9. temperatureinitially and gradually increasing the proportion of acetone to 100%

Quellen und Nachweise

ORD-Eintrag
ord-bd2391ba627a4ac5a81e6a1d58c29243
Quelldatensatz
uspto-grants-1991_09
Patentnummer
US05049497

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