Water → HCID 12507348, compound

HRID 728530Notes

Reaction equation

HRID 728530 reaction equation
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]

Participants

6

Reactant 3

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

Product 2

HCID 12507348HCID 12507348, compoundHCID 14127271HCID 14127271, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
32 °C

Procedure

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).

Workup

  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%

Sources & evidence

ORD record
ord-bd2391ba627a4ac5a81e6a1d58c29243
Source dataset
uspto-grants-1991_09
Patent number
US05049497

Reaction notes

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