Reaktion #162227

Reaktionsgleichung

HCl

6-bromohexahydro-2H-3,5-methanocyclopenta[b]furan-2-one

72a

6-bromohexahydro-2H-3,5-methanocyclopenta[b]furan-2-one

NaOH

→

6-oxonorbornane-2-carboxylic acid

Lösungsmittel

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with Et2O
2. 2
   TrocknenThe organic phase was dried (Na2SO4)
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated in vacuo
5. 5
   SonstigeThe resulting residue was purified by silica gel chromatography (0-20% MeOH/CH2Cl2 gradient)

Vorschrift

6-bromohexahydro-2H-3,5-methanocyclopenta[b]furan-2-one, 72a, (28.0 g, 129.0 mmol) was treated with NaOH (258.0 mL of 2 M solution, 516.0 mmol) in H2O (350 mL) for 2 hour at room temperature. The reaction mixture was acidified with conc. HCl, extracted with Et2O. The organic phase was dried (Na2SO4), filtered and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (0-20% MeOH/CH2Cl2 gradient) to provide 16 g of 6-oxonorbornane-2-carboxylic acid.

Quelle