By Richard S. Monson
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Extra resources for Advanced Organic Synthesis, Methods and Techniques
It may be partially liquid, but it may be recrystallized from petroleum ether affording c/s-4-hydroxycyclohexanecarboxylic acid lactone, mp 125-126°. However, the recrystallization is not necessary for conversion to the hydroxy acid. The lactone (fraction boiling at 220-260°) is dissolved in a minimum amount of water and heated on a steam bath for 2 hours. The cooled solution is extracted six times with small portions of ether (or, preferably, continuously extracted with ether overnight). The ether extracts are dried (anhydrous sodium sulfate), and the ether is evaporated.
The combined extracts are washed three times with 30-ml portions of water and dried over anhydrous magnesium sulfate. 4194, in about 90% yield. REFERENCES 1. N. G. " Interscience, New York, 1956; W. G. Brown, Org. React. 6, 469 (1951). 2. A. I. Vogel, "Practical Organic Chemistry," 3rd ed. Longmans, London, 1956. 3. W. G. Dauben, R. C. Tweit, and R. L. MacLean, /. Amer. Chem. Soc. 77, 48 (1955). 4. A. C. Cope and E. Ciganek, Org. Syn. Collective Vol. 4, 339 (1963). 5. E. L. EHeI, Rec. Chem. Progr.
REFERENCES 1. A. J. Birch, Quart. Rev. 4, 69 (1950); A. J. Birch and H. 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.