Organic Lab Reactions 170

Organic Lab Reactions 170 - (d)...

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THE SULFURIC ACID METHOD 165 general reaction for dicarboxylic acids which are capable of forming cyclic anhydrides, 3-Carboxytetralone-l (LXXX) was thus obtained from benzylsuccinic acid. 196 A similar type of cyclization was reported 196 in the case of the tricarboxylic acid LXXXV. The ring was closed by the action of concentrated sulfuric acid at 0° for forty minutes, but the yield was not recorded. TABLE IX COMPARISON OF YIELDS OBTAINED BY THE SULFTJRIC ACID AND FRIEDEL-CRAFTS METHODS Acids Submitted to Cyclization /3-Phenylpropionic acid (a) 7-Phenylbutyric acid (6) 7-m-Methoxyphenylbutyric acid 7-p-Ethylphenylbutyric acid a,/3,7-Triphenylbutyric acid 7-1-Naphthylbutyric acid (c) 7-2-Naphthylbutyric acid 7-2-Phenanthrylbutyric acid
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Unformatted text preview: (d) 7-(9,10-Dihydro-2-phenanthryl)-butyric acid (c) 7-3-Pyrenylbutyric acid (e) l,2-Benzanthracene-5-acetic acid /3,7-Dianisyladipic acid Best Yields of Ketones Sulfuric Acid 27% 50% 79% 50-55% 25% 70-75% 70-75% 44% 30% 0% 0% 0% Reference 71 15,78 197 15 155 193 193 43 58 80 48 142 Friedel-Crafts 95% 74-91% 96% 87% 58% 81-94% 90% 80-91% 77-90% 85-96% 74% 80% Reference 75 79 14 104 155 95,100 104 43 64,97 38,85 48 142 (a) See Table II. (6) See Table III. (c) See Table V. (d) See Table XIV. (e) See Table IV. 196 Attwood, Stevenson, and Thorpe, / . Chem. Soc, 1923, 1755. 196 Robinson and Thompson, J. Chem. Soc, 1938, 2009. 197 Rapson and Robinson, J. Chem. Soc, 1935, 1285....
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