Organic Lab Reactions 139

Organic Lab Reactions 139 - 50 70 74-91 92 Refer 35 78 15...

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134 THE FORMATION OP CYCLIC KETONES TABLE III CTCLIZATION OF T-PHENYLBTJTYRIC ACID TO TETRALONE-1 Exam- ple 1 2 3 4 5 6 7 g Condensing Agent (a) Aluminum chloride (a) Aluminum chloride 96% Sulf uric acid Concentrated sulf uric acid Concentrated sulfurie acid (a) Aluminum chloride (a) Aluminum chloride Hydrogen fluoride Solvent 70-80° petroleum ether 100-110° petroleum ether Benzene Carbon disulfide Conditions Heat until all hydrogen chlo- ride is evolved Heat until all hydrogen chlo- ride is evolved 100° for 1 hour Water bath (3.5 hours) Water bath (3 hours) (c) Cold Warm for 10 minutes 16 hours at room temperature Yield 10% • (6) 10%* 27% 49%
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Unformatted text preview: 50% 70%* 74-91% 92% Refer-ence 76 77 35 78 15 74 79 16 * Yield based on acid chloride. (a) Friedel-Crafts reaction on the acid chloride. (6) Kipping suggests that the by-product is of the hydrindylidenehydrindone type. (c) Allowed to stand until the evolution of hydrogen chloride became vigorous; then hydrolyied. 74 Mayer and Stamm, Ber., 56, 1424 (1923). " Kipping and Hill, J. Chem. Soc., 1899, 144. 78 Home and Shriner, J. Am. Chem. Soc., 55, 4652 (1933). n Martin and Fieser, Org. Syntheses, Coll. Vol. 2, 669 (1943)....
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