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By Richard S. Monson

ISBN-10: 0125049501

ISBN-13: 9780125049504

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Aminobenzoic acid, 200 ml of water, and 2 g of the catalyst is hydrogenated at 50 psi in a Parr apparatus. 6 mole of hydrogen), the mixture is filtered and concentrated under vacuum. When crystals start to form, the mixture is diluted with 200 ml of DMF and cooled in an ice bath. The crystals are collected by filtration, washed with DMF followed by methanol, and dried. s-4-ammocycloriexanecarboxylic acid, mp 292-296°, are obtained. 3. y-4-aminocyclohexanecarboxylic acid is mixed with 30 ml of Dowtherm At and heated rapidly to reflux in a flask fitted with a short distilling column.

2. 3. 4. 5. 6. I. M. Downie, J. B. Holmes, and J. B. Lee, Chem. lnd. (London), p. 900 (1966). J. B. Lee and I. M. Downie, Tetrahedron 23, 359 (1967). A. W. Friederang and D. S. Tarbell, /. Org. Chem. 33, 3797 (1968). G. A. Wiley, R. L. Hershkowitz, B. M. Rein, and B. C. Chung, /. Amer. Chem. Soc. 86,964 (1964). D. Levy and R. Stevenson, J. Org. Chem. 30, 3469 (1965). J. P. Schaefer, J. G. Higgins, and P. K. Shenov, Org. Syn. 48, 51 (1968). REFERENCES 53 7. C. Djerassi, Chem. Rev. 43, 271 (1948); L.

The flask is flushed with nitrogen and then refluxed for 40 minutes with IV. a-BROMINATION OF KETONES AND DEHYDROBROMINATION 49 stirring. The succinimide is removed by suction filtration and washed twice with 10-ml portions of carbon tetrachloride. The combined filtrate and washings are fractionally distilled at atmospheric pressure to remove the carbon tetrachloride and excess olefin (steam bath). The residue is distilled under vacuum, giving about 60 % yield of 3-bromocyclohexene, bp 68°/15 mm or 44°/2 mm.

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Advanced Organic Synthesis. Methods and techniques by Richard S. Monson


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