By Richard S. Monson
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Extra resources for Advanced Organic Synthesis, Methods and Techniques
Smith, Quart. Rev. 12, 17 (1958). 2. R. A. Benkeser and E. M. Kaiser, /. Org. Chem. 29, 955 (1964). 3. L. Reggel, R. A. Friedel, and I. Wender,/. Org. Chem. 22, 891 (1957); W. G. Dauben, E. C. Martin, and G. J. Fonken, J. Org. Chem. 23, 1205 (1958). 4. G. Stork and S. D. Darling, /. Amer. Chem. Soc. 86, 1761 (1964) and references cited therein. 5. E. E. van Tamelen and W. C. Proost, J. Amer. Chem. Soc. 76, 3632 (1954). 6. M. Yanagita, K. Yamakawa, A. Tahara, and H. Ogura, /. Org. Chem. 20, 1767 (1955).
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). C/s-J2-5,8-OCTALINDIONE (8) O Zn/HOAc 30 3. DISSOLVING METAL REDUCTIONS Six grams of the quinone-butadiene adduct are dissolved in 25 ml of 95% acetic acid and the solution is placed in a round-bottom flask fitted with a thermometer and a mechanical stirrer.
The distillate is extracted with ether, and the extract is dried over anhydrous magnesium sulfate. 0 g (70%) of n-octanal, bp 83-85°/33 mm. B. 15 mole) of d-limonene over a period of 5 minutes. The reaction mixture is allowed to stand at room temperature for approximately 3 hours. It is then oxidized by the addition of 50 ml of 3 TV sodium hydroxide followed by 50 ml of 30% hydrogen peroxide. The alcohol is worked up in the usual manner. Upon distillation, the primary "terpineol" is obtained, bp 115-116°/10 mm.
Advanced Organic Synthesis, Methods and Techniques by Richard S. Monson