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ERIC Number: EJ1069027
Record Type: Journal
Publication Date: 2015-Jul
Pages: 5
Abstractor: As Provided
Reference Count: 20
ISBN: N/A
ISSN: ISSN-0021-9584
Synthesis of a Fluorescent Acridone Using a Grignard Addition, Oxidation, and Nucleophilic Aromatic Substitution Reaction Sequence
Goodrich, Samuel; Patel, Miloni; Woydziak, Zachary R.
Journal of Chemical Education, v92 n7 p1221-1225 Jul 2015
A three-pot synthesis oriented for an undergraduate organic chemistry laboratory was developed to construct a fluorescent acridone molecule. This laboratory experiment utilizes Grignard addition to an aldehyde, alcohol oxidation, and iterative nucleophilic aromatic substitution steps to produce the final product. Each of the intermediates and the acridone product of the synthesis are analyzed by common techniques available in most undergraduate chemistry laboratories such as melting point, thin-layer chromatography, infrared spectroscopy, UV-vis spectroscopy, and fluorescence spectroscopy. Yields for each transformation in the synthesis are generally moderately low to good (20-90%), and nearly all of the students (>90%) who attempted the synthesis were able to produce the final acridone 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: National Center for Research Resources (NIH/DHHS); National Institute of General Medical Sciences (NIH)
Authoring Institution: N/A
IES Grant or Contract Numbers: 5P20RR016464-11|8 P20 GM103440-11