Hydrofluoric Acid → HCID 14486030, compound

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%.

1. additionThe resulting mixture was added dropwise
2. additionThe temperature was kept at about -10° C. during the addition (45 min)
3. additionAfter the addition
4. stirringthe reaction mixture was stirred for a further period of 15 minutes at 0° C.
5. customThe upper layer was then decanted
6. extractionthe aqueous layer was extracted several times with pentane
7. washwashed with water
8. additionThe pentane layer was then treated
9. customresulted in 10.8 g of 1,5-dimethyl-8-fluorobicyclo-[3,2,1]octane (b.p. 68°-69° C./22 mm Hg)

ORD record

ord-79b0ff26919246d2a19cf9afa68780a5

Source dataset

uspto-grants-1980_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04239707