Document Detail

Reaction of Resorcinol with alpha,beta-Unsaturated Ketones.
MedLine Citation:
PMID:  11672054     Owner:  NLM     Status:  Publisher    
Products of the acid-catalyzed reaction of resorcinol with alpha,beta-unsaturated ketones have been found to fall into two classes. The first type of product is illustrated by 4-(3,4-dihydro-7-hydroxy-2,4,4-trimethyl-2H-1-benzopyran-2-yl)-1,3-benzenediol, 1, formed in 91% yield by the reaction of resorcinol with 4-methyl-3-penten-2-one (mesityl oxide). The second type of product is illustrated by (C(2)-symmetric) 2,2'-spirobi(7-hydroxy-4,4-dimethylchroman),4, formed in 85% yield by the reaction of resorcinol with 2,6-dimethyl-2,5-heptadien-4-one (phorone). A number of examples of reactions leading, in quite good yields, to products analogous to 1are presented, as well as some reactions that fail. Flavan 1 is identical to the compound formed by the acid-catalyzed reaction of acetone with excess resorcinol. Compound 1 and a steroidal analogue of 1 have been found to be fluorescent.
P. Livant; Weizheng Xu
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Publication Detail:
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  63     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  1998 Feb 
Date Detail:
Created Date:  2001-Oct-23     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  636-641     Citation Subset:  -    
Department of Chemistry, Auburn University, Auburn, Alabama 36849-5312.
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