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acetal XXXV added dropwise anhydrous ether anhydrous magnesium sulfate anhydrous sodium aqueous layer Attempted Condensation benzene calcium chloride drying chloride drying tube chloroketone XXVI chromatography colorless liquid compound Condensation of Cyclopentadiene crude product cyclopentadiene dienophile diethyl acetal XXXVII dissolved dried with anhydrous drying tube easily mobile liquid ethanol ether was added ether was evaporated ethereal solution extracted three extracted with three glacial acetic acid heptane hydrochloric acid hydrogen infrared spectrum showed ketone liquid remained lithium aluminum hydride longifolene mechanical stirrer Merck Alumina methyl iodide methylated product mixture was extracted ml0 of anhydrous ml0 portions mole neutralized nitromethane nitrosochloride norbornene norcamphor obtained oxidation portions of ether potassium pyridine reaction mixture rearrangement reflux condenser removed by filtration room temperature semicarbazone sodium carbonate sodium hydroxide solvent spectrum had bands starting material sulfuric acid tosylate vacuum-jacketed Vigreux column Vigreux column washed with water white solid XVIII yellow liquid yield