Hydrofluoric Acid → HCID 14486030, compound

Participants

Reaction Steps

A mixture of 13.6 g (0.1 mol) 1,5-dimethyl-1,5-cyclooctadiene and 1,6-dimethyl-1,5-cyclooctadiene (ratio 80/20 was dissolved in a mixture of tetrahydrofuran (15 ml) and methanol (5 ml). The resulting mixture was added dropwise under stirring and cooling to 50 ml anhydrous hydrogen fluoride. The temperature was kept at about -10° C. during the addition (45 min). After the addition, the reaction mixture was stirred for a further period of 15 minutes at 0° C. and then poured into a cooled saturated solution of potassium acetate in water. The upper layer was then decanted and the aqueous layer was extracted several times with pentane. The upper layer and the pentane solutions were combined and washed with water and an aqueous diluted solution of sodium bicarbonate (5%). The pentane layer was then treated as described in Example 1a which resulted in 10.8 g of 1,5-dimethyl-8-fluorobicyclo-[3,2,1]octane (b.p. 68°-69° C./22 mm Hg) or a yield of 86.5% based on the starting 1,5-dimethyl-1,5-cyclooctadiene. The purity of the product according to gas-liquid chromatography was more than 98%.

Provenance & Evidence