Organic Lab Reactions 140

Organic Lab Reactions 140 - (b) Same as (a) except that...

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THE FRIEDEL-CRAFTS METHOD 135 TABLE IV CTCLIZATION or 7-3-PYKBNTLBUTTKIC ACID TO 4'-KETO-1',2',3',4'-' TETRAHYDRO-3,4-BENZPYRENE Exam- ple 1 2 3- 4 5 6 7 8 Condensing Agent P2O5, 80% H 2 SO 4 , POClj, AlClg (o) Zinc chloride Stannic chloride Stannic chloride . (b) Aluminum chloride (a) Stannic chloride (6) Stannic chloride (b) Stannic chloride Solvent Benzene Carbon disulfide Benzene Benzene Conditions Fuse at 180° for 1 hour Fuse at 115-120° for 1 hour Fuse at 110-112° for 1 hour 8 hours at room temperature 3 hours at 0°; 3 hours refluxing 4 hours at room temperature; 4 hours refluxing 8 hours at room temperature Yield All failed 16% 19%- 37% 66% 80-86% { 85-05% 96% Refer- ence 80 80 80 81 82 83 84 38 86 (a) Friedel-Crafts reaction on the acid chloride.
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Unformatted text preview: (b) Same as (a) except that reaction was carried out in the presence of the phosphorus compounds remaining after the formation of the acid ohlonde with phosphorus pentachlonde. 80 Cook and Hewett, J. CKem. Soe., 193S, 398. . H Winterstein, Vetter, and Soh6n, Ber., 68, 1079 (1935). " Vollmann, Becker, Corell, and Streeck, Ann., 531, 1 (1937). " Fieser and Fieser, / . Am. Chem. Soe., 57, 782 (1935). 84 Fieser, Hershberg, Long, and Newman, J. Am. Chem. Soe., 59, 475 (1937). 86 Bachmann, Carmack, and Safir, J. Am. Chem. Soe., 63, 1682 (1941)....
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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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