Organic Lab Reactions 167

Organic Lab Reactions 167 - (g) Lower yield on larger runs....

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162 THE FORMATION OF CYCLIC KETONES TABLE VIII— Continued CYCLIZATIONS WITH HTDBOGEN FLTJOMDB Ring System of Ketones Prepared 4-methyl 2-methyl 2,3-dimethyl 4,5-Meihylenechrysene 0 3,4-Benzpyrene Yields 88% 93% (/) 71% 95% 90% 70% Reference 52 52 186 189 189 89 (a) Acid recovered unchanged, 94%. (6) Reaction conducted in closed container under pressure for five days; 57% acid recovered. (c) Unchanged acid amounted to 34%. (d) Friedel-Crafts and sulfuric acid methods failed to give any ketone (reference 26). (e) Small amount (6%) of 4,5-benzhydrindone-l was isolated, total yield of ketone 87%. (/) Mixture of diastereoisomers.
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Unformatted text preview: (g) Lower yield on larger runs. The Sulfuric Acid Method It has been known for some time 190 that sulfuric acid can be used as an agent for dehydrating 7-arylbutyric and j8-arylpropionic acids to 188 Fieser and- Daudt, J. Am. Chem. Soc., 63, 782 (1941). 187 Johnson and Goldman, unpublished observation. 188 Lothrop and Coffman, J. Am. Chem. Soc., 63, 2564 (1941). 189 Fieser and Cason, /. Am, Chem. Soc., 62, 1293 (1940). * 90 An early instance has been reported by Reimer, Ber., 14, 1802 (1881), and Roser, Ann., 247, 152 (1888)....
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