A two-step synthetic sequence was developed for the undergraduate organic chemistry laboratory using vanillin as the starting material. The multi-step synthesis was designed to replace two traditional experiments teaching electrophilic aromatic substitution and carbon–carbon bond forming chemistries with greener transformations. Vanillin is iodinated using Oxone® and potassium iodide in refluxing water, and students are tasked with determining the position of aromatic substitution using ¹H NMR spectroscopy. The tan, shiny, pleasant-smelling iodovanillin is subsequently used in an aqueous Suzuki-Miyaura reaction with para-methylphenylboronic acid; strategically chosen to afford a second instructive ¹H NMR spectrum. Both conventional heating and microwave conditions can be employed for the palladium-catalyzed reaction. This synthetic sequence, successfully performed over multiple semesters by hundreds of students, models green chemistry principles through the use of a potentially renewable feedstock and safer reagents, the choice of water as a safer reaction solvent, and the employment of a catalytic reaction. Additionally, the sequence minimizes waste in teaching labs through use of an intermediate product.

以香草醛为起始原料，为本科有机化学实验室开发了两步合成序列。设计了多步合成法，以绿色转化代替了两个传统的实验，该实验教导了亲电子芳族取代和形成碳碳键的化学反应。香草醛是使用Oxone®和碘化钾在回流水中进行碘化的，学生的任务是使用¹ H NMR光谱确定芳族取代的位置。棕褐色，发亮，气味宜人的碘香兰素随后用于Suzuki-Miyaura与对甲基苯基硼酸的水溶液反应。战略性地选择提供第二个指导性课程¹1 H NMR谱。常规的加热条件和微波条件均可用于钯催化的反应。数百名学生在多个学期中成功完成了这一合成序列，通过使用潜在的可再生原料和更安全的试剂，选择水作为更安全的反应溶剂以及采用催化反应来模仿绿色化学原理。此外，通过使用中间产品，该顺序最大程度地减少了教学实验室中的浪费。