Cydobutanecarboxylic acid

Cydobutanecarboxylic acid has been prepared by decarboxylation of the 1,1-dibasic acid,1-4 and by decarboxylation of 1-cyano- 1-carboxycyclobutane followed by hydrolysis of the cyano group.2... 

In a 1-1. three-nccked, round-bottomed flask equipped with a mechanical stirrer, reflux condenser, and powder funnel are placed 180 ml. of reagent grade chloroform, 16.0 g. (0.16 mole) of cydobutanecarboxylic acid (Note 1), and 48 ml. of concentrated sulfuric acid. The flask is heated in an oil bath to 45-50°, and 20.0 g. (0.31 mole) of sodium azide (Note 2) is added over a period of 1.5 hours (Note 3). After the addition of sodium azide is complete, the reaction mixture is heated at 50° for 1.5 hours. The flask is cooled in an ice bath, and approximately 200 g. of crushed ice is added slowly. A solution of 100 g. of sodium hydroxide in 200 ml. of water is prepared, cooled to room temperature, and then added slowly to the reaction mixture until the pH of the mixture is approximately 12-13. The mixture is poured into a 2-1. three-necked, round-bottomed flask, the... 

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