Wittig Reaction Using a Stabilized Phosphorus Ylid: An Efficient and Stereoselective Synthesis of Ethyl trans-Cinnamate

Abstract

The synthesis of ethyl trans-cinnamate, by the reaction of benzaldehyde with the stabilized phosphorus ylid (carbethoxymethylene)triphenylphosphorane, serves as a useful experiment to illustrate the Wittig reaction in the introductory organic chemistry laboratory. The reaction is highly stereoselective and affords the product in excellent yield and purity. The stereochemistry of the product is established by examining the coupling constants displayed by the olefinic protons in the 1H NMR spectrum. The experiment highlights several important aspects of organic chemistry such as synthesis, stereochemistry, instrumental analysis, and molecular modeling.

High-yield synthesis of bioactive ethyl cinnamate by enzymatic esterification of cinnamic acid

“…Moreover, ethyl cinnamate is also often used in cosmetic products such as face creams, hair sprays, shampoos and toilet soaps (Belsito et al, 2007;Bhatia et al, 2007). Traditionally, ethyl cinnamate could be extracted from natural materials or synthesized by chemical methods (Nguyen & Weizman, 2007;Speed, McIntyre, & Thamattoor, 2004). However, these ways have many drawbacks such as low productivity and tedious purification steps (Martins et al, 2011), use of hazardous chemicals (Lv, Pan, & Li, 2007), and costly equipment (Yadav & Devendran, 2012).…”

Natural and Synthetic Derivatives of Hydroxycinnamic Acid Modulating the Pathological Transformation of Amyloidogenic Proteins

“…The most common and straightforward methods for the synthesis of cinnamic acid itself is via the Perkin reaction [ 51 ] or Knoevenagel condensation [ 52 ] starting from benzaldehyde ( Figure 2 ). Even though the latter procedure can also be used for the synthesis of HCA derivatives, many other methods for constructing a cinnamoyl moiety have been also developed ( Figure 2 ), e.g., reaction of benzaldehydes with Meldrum’s acid in the presence of catalytic amounts of 2-carbamoylhydrazine-1-sulfonic acid and carbamoylsulfamic acid [ 53 ], Wittig olefination reaction of benzaldehydes [ 54 , 55 ], Heck coupling of aryl halides or benzoic anhydride with alkenes [ 56 ], and straightforward synthesis from aromatic aldehydes, aliphatic carboxylic acids and boron tribromide using 4-dimethylaminopyridine and pyridine as bases [ 57 ]. Here, we will focus only on synthetic methods for the preparation of HCAs and their derivatives.…”

Greening Wittig Reactions: Solvent-Free Synthesis of Ethyl trans-Cinnamate and trans-3- (9-Anthryl)-2-Propenoic Acid Ethyl Ester

“…The synthesis of ethyl trans-cinnamate using a stabilized ylide was published recently (1, Scheme I) (5). The experiment was carried out using methylene chloride as a solvent.…”