Organic Lab Reactions 145

Organic Lab Reactions 145 - in nitrobenzene 24 hours at 0°...

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140 THE FORMATION OF CYCLIC KETONES TABLE V COMPARISON OP YIELDS WITH ALTJMINTTM AND STANNIC CHLORIDE IN THE FRIEDEL-CRAFTS METHOD Acid Condensing Agent and Medium Conditions Yields of Ketones Refer- ence (a) Aluminum chloride in benzene Several hours at room tempera- ture; 1.5 hours reflux 77% (6) Stannic chloride in benzene 1 hour cold 90% 97 64 (6) Aluminum chloride in sym-tetrachlo- roethaae 16 hours at 0° 86% OCH, (b) Stannic chloride in benzene 1 minute cold 92% 99 (a) Aluminum chloride in benzene 6 hours at room temperature 72% (o) Stannic chloride in benzene lS.hours at room temperature 81% 66 89 (o) Aluminum chloride in benzene 12 hours at room temperature, 2.5 hours reflux (c) 81% COaH (6) Stannic chloride in benzene 5 minutes cold 92-94% 100 95 HD 2 C—CHj -CH* (6) Aluminum chloride
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Unformatted text preview: in nitrobenzene 24 hours at 0° 74% (6) Stannic chloride in carbon disulfide 1.5 hours reflux (d) 54% 42 (o) Acid chloride formed with phosphorus pentachloride; phosphorus compounds not removed before addition of condensing agent. (ft) Acid chloride formed with thionyl chloride. (c) Crude distilled ketone. (d) About 17% of unreacted acid was recovered. The yield based upon acid which reacted was 65%. " Fieser and Johnson, J. Am. Chem. Soc, 61, 168 (1939). 98 Kon and F. C. J. Ruzicka, J. Chem. Soc, 1936, 187. 99 Bachmann and Holmes, J. Am. Chem. Soc, 62, 2750 (1940), 100 Drake and McVey, J. Org. Chem., 4, 464 (1939),...
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This note was uploaded on 11/20/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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