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Advanced Organic Synthesis: Methods and Techniques by Richard S. Monson

By Richard S. Monson

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Ergosterol (a triene) rapidly takes up 1 mole of hydrogen selectively to give 5a,6-dihydroergosterol, recrystallized from methanol-chloroform, mp 173-174°. 3. 4261. ) 4. j8-Nitrostyrene requires from 60-90 hours for the uptake of 1 mole of hydrogen. 5 mm. 5. Methyl oleate gives methyl 9,10-dideuterostearate on treatment with deuterium. Similarly, methyl linoleate gives 9,10,12,13-tetradeuterostearate. The products have bp 214-215°/15 mm. 6. 1,4-Naphthoquinone reacts in 30 minutes to give 1,2,3,4-tetrahydro-1,4-dioxonaphthalene in 70% yield.

The flask is fitted with a magnetic stirrer and a short Vigreux column, and the receiving flask is cooled in a Dry Ice-acetone bath. The flask II. THE WOLFF-KISHNER REDUCTION 55 is heated (oil bath, contained in stainless steel or copper) to 90-100° and vacuum (approx. 10 mm) is applied with stirring. Resolidification of the amine oxide indicates loss of the water of hydration. Thereupon, the bath temperature is raised to 160° and decomposition of the amine oxide occurs over about 2 hours. The distillate is mixed with water (100 ml) and the olefin layer is separated.

The product is isolated by distillation of the residue. Examples 1. 6 g of methyl isobutyl ketone, bp 117-118°/l atm and a residue of 3 g. 2. 3 mm, 207°/1 atm. 3. 1-Benzoylcyclohexene gives, after removal of the ether, phenyl cyclohexyl ketone, which is recrystallized from petroleum ether, mp 52° (80%). 4. J1(9)-Octalone-2-gives trans-2-decalone, bp 112-114°/13 mm. V. -unsaturated y-diketones can conveniently be done with zinc in acetic acid. The following procedure is applicable to the reduction of the Diels-Alder adduct of quinone and butadiene (Chapter 8, Section II).

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