NotesFAQContact Us
Search Tips
Peer reviewed Peer reviewed
Direct linkDirect link
ERIC Number: EJ825814
Record Type: Journal
Publication Date: 2008-Mar
Pages: 3
Abstractor: As Provided
Reference Count: 19
ISSN: ISSN-0021-9584
Synthesis and Characterization of 9-Hydroxyphenalenone Using 2D NMR Techniques
Caes, Benjamin; Jensen, Dell, Jr.
Journal of Chemical Education, v85 n3 p413-415 Mar 2008
9-Hydroxyphenalenone is a planar multicyclic [beta]-keto-enol, which is synthesized via a Friedel-Crafts acylation followed by acid-catalyzed intramolecular Michael addition with the loss of a phenyl group in a one-pot reaction during a four-hour lab period. Tautomerization of the [beta]-keto-enol results in C[subscript 2v] symmetry on the NMR time scale, which simplifies the spectra and provides a unique structure for teaching 2D NMR spectroscopy. The [to the first power]H and [to the thirteenth power]C assignments can be made using 1D and 2D NMR techniques and data collection can be reduced to less than twenty minutes with optimized parameters. (Contains 2 figures, 1 scheme, 1 table and 1 note.)
Division of Chemical Education of the American Chemical Society. Subscription Department, P.O. Box 1267, Bellmawr, NJ 08099-1267. Tel: 800-691-9846; Tel: 856-931-5825; Fax: 856-931-4115; e-mail:; Web site:
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A