Aluminum(III) Chloride → HCID 59559135, compound

Temperature

-30 °C

Aluminum chloride (AlCl3, 110 g) was suspended in toluene (1 L) and chilled to −30° C. using a dry ice/isopropanol bath. 2-Propylbicyclo[2.2.1]hept-5-ene-2-carbaldehyde (136 g, synthesized as above) was fed in using an addition funnel over 1 hour while the temperature was maintained at −30° C. After the feed was completed the temperature was allowed to rise to 0° C. GC analysis showed the reaction was completed after 40 minutes. The reaction mixture was then poured onto H2SO4 (1 L, 20%) over ice. The resulting biphasic mixture was shaken to split the organic and aqueous layers. The aqueous layer was washed once with toluene (300 mL) and combined with the organic layers. The mixture was then washed with NaOH solution (750 mL, 10%), followed by water until the water was tested neutral. The resulting organic material was purified by distillation to yield 3-propylbicyclo[3.2.1]oct-6-en-2-one (92 g).

1. customover 1 hour
2. temperaturewas maintained at −30° C
3. customto rise to 0° C
4. additionThe reaction mixture was then poured onto H2SO4 (1 L, 20%) over ice
5. customto split the organic and aqueous layers
6. washThe aqueous layer was washed once with toluene (300 mL)
7. washThe mixture was then washed with NaOH solution (750 mL, 10%)
8. distillationThe resulting organic material was purified by distillation

ORD record

ord-0caca2a046e241c2a3911a4c6d1ad44d

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07842659B2