P. L. Egerton.; E. M. Hyde.; J. Trigg.; A. Payne.; P. Beynon.; M. V. Mijovic.; A. Reiser. Photocycloaddition in liquid ethyl cinnamate and in ethyl cinnamate glasses. The photoreaction as a probe into the micromorphology of the solid. J. Am. Chem. Soc. 1981, 103 (13), 3859-3863.
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Melting Point Study
Theoretical MP 88-89 degrees Celsius
Obtained MP 84-85 degrees Celsius
Concluding - In analyzing the HNMR for the product and our obtained final product, we can confirm that we were able to obtain 4-methoxycinnamate successfully.
- The melting point for our final product was 84 ̊-85 ̊C in which the original product is said to have 88-89 ̊C
- We believe the product in which we used sodium hydroxide as a reagent came out as a liquid was due to the fact that the sodium hydroxide was in liquid form.
Ethyl cinnamate is the ester of cinnamic acid and ethanol
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In an effort to determine the versatility of this experimental protocol when other alkyl halides were employed, bromoacetonitrile was substituted for methyl bromoacetate and then reacted with benzaldehyde. The students synthesized cinnamonitrile and the average yield was calculated to be 56.9 %; the highest yield that was reported for the synthesis of cinnamonitrile was 86.1 %. Cinnamonitrile was synthesized in a stereoselective manner, but the : ratio was severely eroded; Wu observed similar results and suggested that the erosion in stereoselectivity for the Wittig reaction that employed bromoacetonitrile was a result of the less bulky nitrile group. The students then analyzed the IR and 1H NMR spectra of cinnamonitrile. The IR spectrum clearly showed the diagnostic nitrile peak at 2215.73 cm-1. The 1H NMR spectrum displayed the expected signals for the vinylic protons of ()-cinnamonitrile at 5.89 ppm and 7.37 ppm, and the vinylic protons of ()-cinnamonitrile at 5.46 ppm and 7.14 ppm. The coupling constants for the vinylic protons within ()-cinnamonitrile and ()-cinnamonitrile were 16.7 Hz and 12.1 Hz, respectively. Although the stereoselectivity of this specific example was poor it was an excellent opportunity for the students to observe the effects of varying just one component of a stereoselective Wittig reaction.
Wittig Reaction - Organic Chemistry Portal
Recently, Bergdahl and coworkers  reported an aqueous Wittig reaction that could be performed in the sophomore organic chemistry laboratory. The reaction was amenable to a variety of aldehydes, and the products were synthesized in poor to excellent yields. In addition, the reaction could be completed within 30 minutes. However, the conditions for this reaction did not adhere to the principles of green chemistry; the aqueous solution had to be refluxed to afford the desired products, the reaction was performed on a multi-gram scale that resulted in a copious amount of waste, and two equivalents of ethyl bromoacetate was required to access the products.
A Useful Base for Organic Synthesis D
(2015) Synthesis and Characterization of Two Novel Biological-Based Nano Organo Solid Acids with Urea Moiety and Their Catalytic Applications in the Synthesis of 4,4’- (Arylme-Thylene)Bis(1H-Pyrazo-5-ol), Coumarin3-Carboxylic Acid, and Cinnamic Acid Derivatives under Mild and Green Conditions.
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Caiding Xu.; Guoying Chen.; Chong Fu.; Xian Huang. The Wittig Reaction of Stable Ylide with Aldehyde Under Microwave Irradiation: Synthesis of Ethyl Cinnamates. Synthetic Communications: An International Journal for Rapid Communication of Synthetic Organic Chemistry. 1995, 25 (15), 2229-2233.