Chemical Properties
white to yellowish crystalline solid
Uses
Titrimetric determination of small amounts of water.
Synthesis
General procedure for the synthesis of 3-phenyl-2-propenyl chloride from trans-cinnamic acid: trans-cinnamic acid (1.0 mmol) was mixed with excess thionyl chloride (5 mL) and reacted at reflux for 2 hours. After completion of the reaction, the excess thionyl chloride was removed by vacuum concentration to obtain 3-phenyl-2-propenyl chloride in quantitative yield.
Purification Methods
Refractionate it in a vacuum until the distillate solidifies on cooling, and recrystallise it from pet ether. The trans-amide has m 145-150o (from H2O) [Beilstein 9 III 2711]. [Adams & Ulich J Am Chem Soc 42 605 1920, Bergmann et al. J Chem Soc 2524 1952, Beilstein 9 H 587, 9 I 233, 9 II 390, 9 III 2710, 9 IV 2020.]
References
[1] Tetrahedron, 2009, vol. 65, # 42, p. 8690 - 8696
[2] Chinese Chemical Letters, 2013, vol. 24, # 8, p. 673 - 676
[3] Molecules, 2016, vol. 21, # 1,
[4] Journal of the American Chemical Society, 2017, vol. 139, # 23, p. 7745 - 7748
[5] Patent: WO2007/141389, 2007, A1. Location in patent: Page/Page column 62
