Sulfuric Acid → Methyl 6-(3-carboxybicyclo[2.2.1]hept-2-yl)-hex-5-enoate

Participants

Reaction Conditions

Reaction Steps

14.5 ml of Jones solution (26.7 g of chromium trioxide and 23 ml of concentrated H2SO4 made up to 100 ml with water) are allowed to run into a solution of 1.2 g (5 mmol) of methyl 6-(3-hydroxymethyl-bicyclo[2.2.1]hept-2-yl)-hex-5-enoate in 250 ml of absolute acetone at -20° C. The mixture is stirred at -20° C. for 3 hours and 40 ml of 2-propanol, followed by 30 ml of water, are then added and the pH is brought to 4 with solid NaHCO3. The precipitate is decanted off, the solution is evaporated in vacuo and the residue is extracted 3 times with ethyl acetate. After the ethyl acetate phase has been dried over sodium sulphate, it is evaporated in vacuo and the methyl 6-(3-carboxybicyclo[2.2.1]hept-2-yl)-hex-5-enoate is purified as described under (a). 1.0 g (yield: 75%).

Provenance & Evidence