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ERIC Number: EJ1062175
Record Type: Journal
Publication Date: 2015-Mar
Pages: 4
Abstractor: As Provided
Reference Count: 7
ISBN: N/A
ISSN: ISSN-0021-9584
Preparation of an Ester-Containing Grignard Reagent by Halogen-Metal Exchange
Snider, Barry B.
Journal of Chemical Education, v92 n3 p553-556 Mar 2015
In this experiment, students carry out a halogen-metal exchange reaction of methyl 2-iodobenzoate with isopropylmagnesium chloride in THF at 0°C to afford 2-carbomethoxyphenylmagnesium chloride, which is treated with "p"-methoxybenzaldehyde to give a lactone (phthalide) product. This reaction introduces students to the modern method of preparation of Grignard and organolithium reagents by halogen-metal exchange rather than by using metallic magnesium or lithium, which is rarely done in a research laboratory. It also demonstrates that Grignard reagents bearing reactive functionality can be prepared and utilized in synthesis, although students are still often taught otherwise. The IR spectrum of the crude product provides semiquantitative information on the success of the reaction because the lactone product and starting material ester and aldehyde have very different carbonyl absorptions, demonstrating the power of this technique to distinguish between functional groups. The product can be purified by chromatography, recrystallization, or trituration, which allows students to compare different purification methods in terms of time required, yield, and purity of product.
Division of Chemical Education, Inc and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education; Postsecondary Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A