Synthesis
General procedure for the synthesis of hydrocinnamoyl chloride from hydrogenated cinnamic acid: To a 200 mL flask equipped with a stir bar and an argon inlet septum were added hydrogenated cinnamic acid (5.00 g, 33.3 mmol), N,N-dimethylformamide (DMF, 0.1 mL), and dichloromethane (CH2Cl2, 30 mL). Oxalyl chloride ((COCl)2, 2 M in CH2Cl2, 20.0 mL, 40.0 mmol) was slowly added to the resulting solution over 30 min. The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the solvent was removed by vacuum concentration to afford 3-phenylpropionyl chloride (74, 5.9 g, yellow oil) in 100% yield. The purity of the product was confirmed to be 99% by high performance liquid chromatography (HPLC) analysis (mobile phase ratio: water:acetonitrile:methanol = 15:10:75) with a retention time of 5.3 min.
References
[1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 10, p. 2899 - 2903
[2] Patent: WO2013/101911, 2013, A2. Location in patent: Page/Page column 57
[3] Arkivoc, 2018, vol. 2018, # 5, p. 334 - 347
[4] Advanced Synthesis and Catalysis, 2015, vol. 357, # 18, p. 3825 - 3830
[5] Journal of the American Chemical Society, 1980, vol. 102, # 20, p. 6311 - 6314
