[Cl-].[Al+3].[Cl-].[Cl-].[CH2:5]([C:12]1([CH:19]=[O:20])[CH2:17][CH:16]2[CH2:18][CH:13]1[CH:14]=[CH:15]2)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].S(=O)(=O)(O)O>C(Cl)Cl>[CH2:5]([CH:12]1[CH2:17][CH:16]2[CH2:15][CH:14]([CH:13]=[CH:18]2)[C:19]1=[O:20])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]Aluminum chloride (279 g, 2 mol) was dissolved in one liter of methylene chloride in a three liter flask and cooled to 0° C. Structure III (909 g, 4.1 mol) was loaded into an addition funnel and fed into the reaction flask while maintaining this temperature. After two hours the reaction was complete as shown by GC measurements. The reaction mixture was then poured onto ice and 10% sulfuric acid, and the organic layers were separated and washed once with 10% sodium hydroxide solution. The methylene chloride solvent was then removed under reduced pressure, and the resulting oil was purified by simple distillation to yield 260 g (28% yield) of IV. Structure IV, 3-heptylbicyclo[3.2.1]oct-6-en-2-one, possesses weak, methyl salicylate like and slightly fruity fragrance notes.
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