Lutjen Andrew B, Quirk Mackenzie A, Kolonko Erin M
Department of Chemistry and Biochemistry, Siena College.
Department of Chemistry and Biochemistry, Siena College;
J Vis Exp. 2018 Oct 30(140). doi: 10.3791/58803.
The Steglich esterification is a widely-used reaction for the synthesis of esters from carboxylic acids and alcohols. While efficient and mild, the reaction is commonly performed using chlorinated or amide solvent systems, which are hazardous to human health and the environment. Our methodology utilizes acetonitrile as a greener and less hazardous solvent system. This protocol exhibits rates and yields that are comparable to traditional solvent systems and employs an extraction and wash sequence that eliminates the need for the purification of the ester product via column chromatography. This general method can be used to couple a variety of carboxylic acids with 1° and 2° aliphatic alcohols, benzylic and allylic alcohols, and phenols to obtain pure esters in high yields. The goal of the protocol detailed here is to provide a greener alternative to a common esterification reaction, which could serve useful for ester synthesis in both academic and industrial applications.
施陶丁格酯化反应是一种广泛用于由羧酸和醇合成酯的反应。虽然该反应高效且温和，但通常使用氯化溶剂或酰胺溶剂体系进行，这些体系对人类健康和环境有害。我们的方法使用乙腈作为更绿色、危害更小的溶剂体系。该方案的反应速率和产率与传统溶剂体系相当，并采用了萃取和洗涤步骤，无需通过柱色谱法纯化酯产物。这种通用方法可用于将各种羧酸与伯醇和仲脂肪醇、苄醇和烯丙醇以及酚类偶联，以高产率获得纯酯。此处详述的方案目标是为常见的酯化反应提供一种更绿色的替代方法，这在学术和工业应用中的酯合成中可能会有用。
