Uses
1-Phenyl-1-cyclopropanecarboxylic Acid, is an intermediate in the synthesis of pharmaceutical products including inhibitors and anticancer compounds. It is also used as the starting material in the synthesis of 2-(1-Phenylcyclopropyl)-4-oxazolecarboxylic Acid (P319785).
Synthesis
Step (vi): synthesis of 1-phenylcyclopropanecarboxylic acid Experimental Procedure: to a solution of 1-phenylcyclopropanecarbonitrile (7 g, mmol) was added water (15 mL), acetic acid (15 mL), and concentrated sulfuric acid (15 mL) sequentially. The reaction mixture was refluxed at 110 °C overnight. After completion of the reaction, the mixture was cooled to room temperature and extracted with ethyl acetate (3 x 50 mL). The organic layers were combined, washed with saturated sodium chloride solution (2 x 50 mL) and dried over anhydrous sodium sulfate. After filtration, the organic phase was concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography (230-400 mesh) with 5% ethyl acetate/hexane mixture as eluent, the target component was collected, and 1-phenylcyclopropanecarboxylic acid was obtained as a colorless solid after concentration under reduced pressure (4.35 g, 50% yield).
References
[1] Pharmaceutical Chemistry Journal, 1980, vol. 14, # 2, p. 114 - 118
[2] Khimiko-Farmatsevticheskii Zhurnal, 1980, vol. 14, # 2, p. 40 - 45
[3] European Journal of Medicinal Chemistry, 1991, vol. 26, # 2, p. 125 - 128
[4] Patent: WO2012/12410, 2012, A2. Location in patent: Page/Page column 46-47
[5] Journal of Organic Chemistry, 1959, vol. 24, p. 616,618, 619
