Nitration%2520Methyl%2520Benzoate.27Aug2007

Nitration%2520Methyl%2520Benzoate.27Aug2007 - Synthesis of...

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Synthesis of Methyl m -Nitrobenzoate (methyl 3-nitrobenzoate ) Courtesy of Dr. Glenn Nomura With minor modifications by Dr. David Jeffrey February 1, 2010 References : 1. Kamm; Segur Organic Synthesis, Collective Vol I , Wiley: New York, 1941, p 369 2. Williamson, Macroscale and Microscale Organic Experiments , 5 th edition, Houghton Mifflin: New York, 2003, Experiment 28.2, Macroscale Nitration of Methyl Benzoate at 1/3 rd of Williamson’s macroscale, p. 433 Equation : Materials : 1. methyl benzoate 1, 2.0 g (0.0147 mol) 2. conc. H 2 SO 4 , 4.0 mL 3. 50:50 mixture of conc. H 2 SO 4 and HNO 3 , 2.5 mL containing 1.25 mL each acid 4. methanol Procedure : Into a clean dry 50 mL Erlenmeyer flask or equivalent reactor fitted with a Teflon stir bar is placed 4.0 mL of concentrated sulfuric acid cooled to 0°C and 2.0 g of methyl benzoate 1 ( note A ). The mixture is cooled by means of an ice bath slush to 0 - 10°C. To this solution is added dropwise during several minutes, 2.5 mL of a mixture of 1.25 mL conc. H 2 SO 4 and 1.25 mL HNO 3 ( note B ). During the dropwise addition, the temperature of the reaction should be kept within the range 5 - 15°C ( note C ). After the nitric/sulfuric acid mixture has been added, stirring is continued for fifteen minutes longer with continued cooling. The mixture is then poured directly in one portion onto 15 g (ca. 30 mL) of cracked ice (
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