Document Detail


On the Kolbe-Schmitt synthesis of pharmacologically useful salicylates: carboxylation of 2,4-di-t-butylphenol and identification and reduction of the formation of 2,2'-dihydroxy-3,3',5,5'-tetra-t-butylbiphenyl in the synthesis of 3,5-di-t-butylsalicylic acid.
MedLine Citation:
PMID:  1791546     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The initial yield of 3,5-di-t-butylsalicylic acid obtained via Kolbe-Schmitt carboxylation of the potassium salt of 2,4-di-t-butylphenol was less than 1% and was accompanied by a 65% yield of 2,2'-dihydroxy-3,3',5,5'- tetra-t-butylbiphenyl, a dimer of the 2,4-di-t-butylphenol formed by ortho coupling of phenoxide radicals. Formation of this dimer was decreased to 8%, and the yield of 3,5-di-t-butylsalicylic acid was increased to 68% by optimizing reaction time and temperature and decreasing the amount of oxygen present during carboxylation. This modification of the Kolbe-Schmitt reaction conditions may be generally helpful in the synthesis of all pharmacologically useful salicylates.
Authors:
M V Chidambaram; J R Sorenson
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Journal of pharmaceutical sciences     Volume:  80     ISSN:  0022-3549     ISO Abbreviation:  J Pharm Sci     Publication Date:  1991 Aug 
Date Detail:
Created Date:  1992-04-01     Completed Date:  1992-04-01     Revised Date:  2000-12-18    
Medline Journal Info:
Nlm Unique ID:  2985195R     Medline TA:  J Pharm Sci     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  810-1     Citation Subset:  IM    
Affiliation:
Division of Medicinal Chemistry, College of Pharmacy, University of Arkansas for Medical Sciences, Little Rock 72205.
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MeSH Terms
Descriptor/Qualifier:
Biphenyl Compounds / chemical synthesis*
Oxidation-Reduction
Phenols / chemical synthesis*,  chemistry
Salicylates / chemical synthesis*,  chemistry
Salicylic Acids / chemical synthesis*
Temperature
Chemical
Reg. No./Substance:
0/Biphenyl Compounds; 0/Phenols; 0/Salicylates; 0/Salicylic Acids; 19715-19-6/3,5-di-tert-butylsalicylic acid; 6390-69-8/2,2'-dihydroxy-3,3',5,5'-tetra-tert-butylbiphenyl; 96-76-4/2,4-di-tert-butylphenol

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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