Organic Lab Reactions 138

Organic Lab Reactions 138 - (6) Procedure same as in...

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THE FRIEDEDOBAFT8 METHOD TABLE II CYCMZATION OF JS-PHENTLPROPIONIC Acm TO HYDRINDONB-1 133 Exam- ple 1 . 2 3 4 5 6 i 7 8 9 10 11 Condensing Agent Concentrated sulfuric acid Concentrated sulfuric acid 5% Fuming sulfuric acid (a) Aluminum chloride Hydrogen fluoride Chloroacetic anhydride (a) Aluminum chloride (a) Aluminum chloride (a) Aluminum chloride (a) Aluminum chloride (a) Aluminum chloride Solvent -60-70° petroleum ether Anisole Petroleum ether Petroleum ether Petroleum ether Benzene 60-70° petroleum ether Conditions Warm 130° for 15 minutes 140° for S'minutes Heat 20-30 minutes 26 hours at 20° 170° for 48 hours Heat only a few minutes Cold (6) Reaction over in a few seconds \ (c) (d) Cold (d) Warmed until complex dis- solved Yield 0% 10% 27% 55-60%* 73% 74% 75%* '80% 90%* 90%* 95%* Refer- ence 69 70 71 65 72 16 73 67 68 20 74 76 * Yield based on acid chloride. (a) Friedel-Crafts reaction on the acid chloride.
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Unformatted text preview: (6) Procedure same as in example 7, except that purer acid chloride was used. A noticeable increase in the rate of reaction was thus brought about. (c) Reaction was vigorous in the cold. (d) The reaction was run inversely in that the acid chloride was added to the mixture of aluminum chloride in petroleum ether. 69 Miller and Rohde, Ber., 33, 1887 (1890). 70 Speight, Stevenson, and Thorpe, J. Chan. Soe., 1924, 2185. 71 Price and Lewis, / . Am. Chem. Soe., 61, 2553 (1939). 71 Revis and Kipping, J. Chem. Soe., 1897, 238. 78 Unger, Ann., 504, 267 (1933). "Amagat, Bull. soe. chim., [4] 41, 940 (1927). "Thiele and Wanscheidt, Ann., 376, 269 (1910)....
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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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