Pinacol-Pinacolone Rearrangement of 1, 2-Di-(p-methoxyphenyl)-ethane-1, 2-diol and Bis-(4-methoxyphenyl)-acetaldehyde in Acid Media

Autor:	Abdul-Aziz Amine Helmy, Sami Bassili Awad, Alfy Badie Sakla, Wadie Tadros
Rok vydání:	1972
Předmět:	Pinacol Organic Chemistry Diol Acetaldehyde Oxide Biochemistry Catalysis Inorganic Chemistry chemistry.chemical_compound Acetic anhydride chemistry Boiling Drug Discovery Pinacolone Organic chemistry Physical and Theoretical Chemistry
Zdroj:	Helvetica Chimica Acta. 55:2808-2812
ISSN:	1522-2675 0018-019X
DOI:	10.1002/hlca.19720550810
Popis:	1, 2-Di-(p-methoxyphenyl)-ethane-1, 2-diol gave in acid media bis-(4-methoxy-phenyl)-acetaldehyde, 4-4′-dimethoxy-deoxybenzoin, and 1, 2-di-(p-methoxyphenyl)-ethylene oxide; their respective yields being influenced by at least 3 factors: (i) the acid, (ii) its concentration, and (iii) the reaction period. Bis-(4-methoxyphenyl)-acetaldehyde rearranged to the deoxybenzoin in boiling sulfuric (50%) or phosphoric (75%) acids (w/w), and to two isomeric 1, 2-diacetoxy-1, 2-di-(p-methoxyphenyl) ethanes when it was heated with acetic anhydride. The mechanisms of these reactions are discussed.
Databáze:	OpenAIRE
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