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Pinacol‐Pinacolone Rearrangement of 1, 2‐Di‐( p‐methoxyphenyl )‐ethane‐1, 2‐diol and Bis‐(4‐methoxyphenyl)‐acetaldehyde in Acid Media
Author(s) -
Tadros Wadie,
Sakla Alfy Badie,
Awad Sami Bassili,
Helmy AbdulAziz Amine
Publication year - 1972
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19720550810
Subject(s) - chemistry , acetaldehyde , acetic anhydride , diol , acetic acid , medicinal chemistry , pinacol , sulfuric acid , phosphoric acid , ethylene , organic chemistry , boiling , ethylene oxide , ethanol , catalysis , polymer , copolymer
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.