Training Undergraduate Sophomores in the Scale-up Reaction Skill with Improved Preparation of (1S)-(+)-Ketopinic Acid: An Organic Chemistry Laboratory Exercise

Abstract

This hands-on experiment trains undergraduate sophomores in scaling up organic reactions while improving the synthesis of (1S)-(+)-ketopinic acid. A two-step method starting from (1S)-(+)-10-camphorsulfonic acid is used, achieving an 80% yield and providing a safer, more efficient approach. Students develop key skills, including understanding optimized reaction conditions, large-scale synthesis techniques, and safe laboratory practices, by utilizing cyanuric chloride as an alternative to thionyl chloride. The experiment integrates theoretical concepts with practical applications, emphasizing green chemistry principles and handling reactions on a scale exceeding 50 g. This activity enhances students’ technical expertise, problem-solving abilities, and understanding of organic synthesis, preparing them for advanced academic and research endeavors. The detailed protocol ensures its suitability for undergraduate organic chemistry laboratories.