a) To a solution of 10 g (60 mmol) of 3-nitrophenylacetic acid in 120 ml of ethanol were added 20 ml of a saturated 5 solution of hydrogen chloride in ethyl acetate and the mixture was heated at reflux for 4 hours, cooled and left to stand at room temperature for 18 hours. The mixture was evaporated and the residue was partitioned between 120 ml of diethyl ether and 100 ml of saturated aqueous sodium 10 bicarbonate solution. The organic phase was dried over magnesium sulfate, filtered and evaporated to give 10.3 g. (82%) of ethyl 3-nitrophenylacetate as a pale yellow oil. [NMR spectrum (250 MHz) 81.25(t) (3H), 83.68(s) (2H), 84.6(q) (2H), 86.5-86.7(m) (3H), 87.09(dd) (1H)].

a) To a solution of 10 g (60 mmol) of 3-nitrophenylacetic acid in 120 ml of ethanol were added 20 ml of a saturated 5 solution of hydrogen chloride in ethyl acetate and the mixture was heated at reflux for 4 hours, cooled and left to stand at room temperature for 18 hours. The mixture was evaporated and the residue was partitioned between 120 ml of diethyl ether and 100 ml of saturated aqueous sodium 10 bicarbonate solution. The organic phase was dried over magnesium sulfate, filtered and evaporated to give 10.3 g. (82%) of ethyl 3-nitrophenylacetate as a pale yellow oil. [NMR spectrum (250 MHz) 81.25(t) (3H), 83.68(s) (2H), 84.6(q) (2H), 86.5-86.7(m) (3H), 87.09(dd) (1H)].

Introduction to General, Organic and Biochemistry

11th Edition

ISBN:9781285869759

Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres

Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres

Chapter19: Carboxylic Anhydrides, Esters, And Amides

Section: Chapter Questions

Problem 19.45P

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