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0 °C

Under an argon atmosphere a stirred suspension of 36.7 grams (0.275 mole) of aluminum chloride in 225 mL of carbon disulfide was cooled to 0° C., and 22.7 mL (0.25 mole) of cyclopropanecarboxylic acid chloride was added dropwise during a 15 minute period. During the addition and for 30 minutes after its completion the reaction mixture temperature was maintained at 0°-15° C. Then 34.8 mL of ethoxybenzene was added dropwise during a one hour period. The reaction mixture temperature was maintained at 5°-10° C. during this addition. Upon completion of addition, the reaction mixture was allowed to warm to ambient temperature as it stirred for one hour. Petroleum ether, 250 mL, was added to the reaction mixture, and the suspension was stirred for ten minutes. The solid was collected by filtration and washed with petroleum ether. The solid was returned to the reaction vessel and, with stirring, was cooled to 0°-10° C. while 50 mL of water was added dropwise during a 30 minute period. Upon completion of addition, the mixture was stirred until the evolution of hydrogen chloride ceased. An additional 250 mL of water was then added, and the mixture was stirred at ambient temperature for 30 minutes. It was then warmed to 80° C. where it stirred for an additional 30 minutes. The mixture was cooled, and a solid was collected by filtration. The solid was dissolved in methylene chloride, and the solution was dried with sodium sulfate. The mixture was filtered, and the filtrate was concentrated under reduced pressure to a residual solid. The solid was recrystallized from heptane, yielding, in two crops, 44.0 grams of cyclopropyl (4-ethoxyphenyl) ketone, m.p. 67°-70° C. The nmr spectrum was consistent with the proposed structure.

1. additionDuring the addition
2. temperaturefor 30 minutes after its completion the reaction mixture temperature was maintained at 0°-15° C
3. temperatureThe reaction mixture temperature was maintained at 5°-10° C. during this addition
4. additionUpon completion of addition
5. temperatureto warm to ambient temperature as it
6. stirringthe suspension was stirred for ten minutes
7. filtrationThe solid was collected by filtration
8. washwashed with petroleum ether
9. stirringwith stirring
10. temperaturewas cooled to 0°-10° C. while 50 mL of water
11. additionwas added dropwise during a 30 minute period
12. additionUpon completion of addition
13. stirringthe mixture was stirred until the evolution of hydrogen chloride
14. additionAn additional 250 mL of water was then added
15. stirringthe mixture was stirred at ambient temperature for 30 minutes
16. temperatureIt was then warmed to 80° C. where it
17. stirringstirred for an additional 30 minutes
18. temperatureThe mixture was cooled
19. filtrationa solid was collected by filtration
20. dissolutionThe solid was dissolved in methylene chloride
21. dry with materialthe solution was dried with sodium sulfate
22. filtrationThe mixture was filtered
23. concentrationthe filtrate was concentrated under reduced pressure to a residual solid
24. customThe solid was recrystallized from heptane