General Description
Cyclopropane-1,1-dicarboxylic acid is a dicarboxylic acid. Cyclopropane-1,1-dicarboxylic acid, an inhibitor of 1-aminocyclopropane-1-carboxylic acid oxidase, was quantitated in Lycopersicum esculentum by HPLC-electrospray tandem mass spectrometry. Crystal and molecular structure of cyclopropane-1,1-dicarboxylic acid has been reported.
Synthesis
GENERAL STEPS: 15 g of diethyl malonate was dissolved in 187 ml of aqueous solution containing 50 μl NaOH at room temperature. Subsequently 21.3 g (93.8 mmol) of benzyltriethylammonium chloride was added and the resulting mixture was stirred for 10 minutes. To the reaction solution was added 12.3 g (65.47 mmol) of 1,2-dibromoethane and the reaction mixture continued to be stirred at room temperature for more than 18 hours. Upon completion of the reaction, the reaction mixture was neutralized by adding acid solution dropwise. The reaction mixture was washed with aqueous sulfuric acid solution and subsequently extracted with ethyl acetate. The organic phases were combined and the solvent was removed by distillation under reduced pressure to afford 6.2 g of a white solid product, 1,1-cyclopropanedicarboxylic acid, in 76.1% yield.
Purification Methods
Recrystallise the di-acid from CHCl3, EtOAc or *C6H6/Et2O/pet ether. It forms a monohydrate. [Nicolet & Satler J Am Chem Soc 49 2070 1927, Beilstein 9 II 512, 9 III 3795.]
References
[1] Organic Letters, 2015, vol. 17, # 11, p. 2618 - 2621
[2] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 16, p. 3353 - 3358
[3] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 24, p. 6674 - 6679
[4] Mendeleev Communications, 2014, vol. 24, # 6, p. 345 - 345
[5] Patent: WO2005/79812, 2005, A1. Location in patent: Page/Page column 51
