Acetic Anhydride → HCID 66747175, compound

Temperature

92.5 °C

To cyclooctene (300 g, 2.73 mol) were added acetic anhydride (556 g, 5.45 mol) and zinc chloride (30 g, 0.22 mol). The reaction mixture was warmed to 90-95° C. within 30 min., stirred at that temperature during 7.5 hours, cooled to 60° C., and treated with caution, within 10 min., with water (400 ml). The resulting mixture was heated at 100° C. during 3 h., cooled to 25° C., and extracted with hexane (3×300 ml). The combined organic phases were washed with aq. sat. NaCl soln. (800 ml), aq. sat. NaHCO3 soln. (800 ml), aq. sat. NaCl soln. (400 ml), and dried (Na2SO4). Evaporation of the solvent led to 375 g of crude material which was distilled under vacuum with a short-path Vigreux column. After collecting the unreacted cyclooctene (65 g, 21.7%) at 40-50° C./100 mbar, the fractions distilling at 110° C./24 mbar were collected (144 g) and redistilled using a microdistillation column (20×1.5 cm, filled with 3×3 mm rolled wire netting) to give 110 g of 1-cyclooct-3-enylethanone (34% based on the reacted cyclooctene, 109° C./20 mbar) as colourless oil.

1. temperaturecooled to 60° C.
2. temperatureThe resulting mixture was heated at 100° C. during 3 h.
3. temperaturecooled to 25° C.
4. extractionextracted with hexane (3×300 ml)
5. washThe combined organic phases were washed with aq. sat. NaCl soln
6. dry with material(400 ml), and dried (Na2SO4)
7. customEvaporation of the solvent
8. distillationwas distilled under vacuum with a short-path Vigreux column
9. customAfter collecting the unreacted cyclooctene (65 g, 21.7%) at 40-50° C./100 mbar
10. distillationthe fractions distilling at 110° C./24 mbar
11. customwere collected (144 g)
12. distillationredistilled
13. additiona microdistillation column (20×1.5 cm, filled with 3×3 mm rolled wire netting)

ORD record

ord-66f306ad8b744257996c777b6986e2a9

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07605118B2