A Phenylglutaric acid

In a 500-mI. flask equipped with a reflux condenser are placed 48.4 g. (0.20 mole) of a-phenyl-a-carbethoxyglutaronitrile/ 225 ml. of hydrochloric acid (sp. gr. 1.19), and 50 ml. of acetic acid. The mixture is heated under reflux for 10 hours. The solution is cooled, transferred to a 1-1. separatory funnel, and diluted with 300 ml. of water. The a-phenylglutaric acid is extracted with five 100-ml. portions of ether-ethyl acetate (1 1) (Note 1). The extracts are combined, washed once with saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvents are removed as completely as possible by distillation from a steam bath, and the residue is transferred to a 200-ml. flask. Acetic anhydride (50 ml.) is added, and the solution is heated under gentle reflux for 1 hour. The excess acetic anhydride is removed by distillation at atmospheric pressure, and the residue is distilled under reduced pressure through a short (15-cm.) Vigreux column with an air-cooled side arm. The product is collected at 178-188°/0.5-l mm. (Note 2). The yield is 31.1-32.7 g. (82-86%) m.p. 90-94°. 

Dehydration, of chloroacetamide, 22 of fumaramide, 46 of frons-methylstyrylcarbinol, 76 a-phenylglutaric acid to a-phenylglu-taric anhydride, 82... 

Phenylacetylene, 72 /ra X-TPHENYL-l,3-BUTAniENE, 75 a-PHENYL-a-CARBETHOXYGLUTARO-NITRILE, 80, 82 0-Phenylenediamine, 56, 86 a-Phenylglutaric acid, 82 a-PHENYLGLUTARIC ANHYDRIDE, 81 Phenylhydrazine, 90 Phenylmagnesium bromide, 97 Phenylsuccinic acid, 83 Phenylsuccinic anhydride, 85 Phosphoric acid, ortho-, 33, 34 Phosphoric anhydride, 33 Phosphorus oxychloride, Tl Phosphorus pentoxide, 22, 46 Potassium, 19, 20 directions for safe handling of, 20 Potassium lerl.-butoxide, solution of, 19... 

PhENYLENE CARBONATE, 33, 74 o-Phenylenediamine, 30, 56, 86 a-Phenylglutaric acid, 30, 82 a-PlIENYLGLUTARIC ANHYDRIDE, 30, 81 Phenyl glycidyl ether, 31, 3 Phenylhydrazine, 30, 90 2-Phenyl-2-hydroxyethane-l-sulfonate, 34, 89... 

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