Pedagogical Comparison of Five Reactions Performed under Microwave Heating in Multi-Mode versus Mono-Mode Ovens: Diels–Alder Cycloaddition, Wittig Salt Formation, E2 Dehydrohalogenation To Form an Alkyne, Williamson Ether Synthesis, and Fischer Esterification

2014 ◽  
Vol 91 (10) ◽  
pp. 1720-1724 ◽  
Author(s):  
Marsha R. Baar ◽  
William Gammerdinger ◽  
Jennifer Leap ◽  
Erin Morales ◽  
Jonathan Shikora ◽  
...  
Keyword(s):  
Microwave Heating ◽  
Diels Alder ◽  
Salt Formation ◽  
Mode Versus ◽  
Fischer Esterification ◽  
Ether Synthesis ◽  
Multi Mode ◽  
Williamson Ether Synthesis

scholarly journals Unexpected course of a Williamson ether synthesis

ARKIVOC ◽  
2006 ◽  
Vol 2007 (7) ◽  
pp. 291-300
Author(s):  
Klaus-Peter Zeller ◽  
Peter Haiss ◽  
Meike Hartmann ◽  
Klaus Eichele
Keyword(s):  
Ether Synthesis ◽  
Williamson Ether Synthesis

EuFOD-Catalyzed Hetero-Diels—Alder (HDA) Reaction under Microwave Heating.

ChemInform ◽  
2007 ◽  
Vol 38 (47) ◽  
Author(s):  
Mauro Panunzio ◽  
Elisa Bandini ◽  
Antonio D'Aurizio ◽  
Alessia Millemaggi ◽  
Zhining Xia
Keyword(s):  
Microwave Heating ◽  
Diels Alder

Dimethyl sulfoxide as a solvent in the Williamson ether synthesis

1969 ◽  
Vol 47 (11) ◽  
pp. 2015-2019 ◽  
Author(s):  
Russel G. Smith ◽  
Alan Vanterpool ◽  
H. Jean Kulak
Keyword(s):  
Reaction Time ◽  
Dimethyl Sulfoxide ◽  
Butyl Alcohol ◽  
Major Product ◽  
Hydroxyl Groups ◽  
Reaction Products ◽  
Butyl Chloride ◽  
Butyl Ether ◽  
Ether Synthesis ◽  
Williamson Ether Synthesis

Using the conventional Williamson ether synthesis, n-butyl ether was prepared from sodium hydroxide, n-butyl alcohol, and n-butyl chloride using excess of the alcohol as solvent in 61% yield after 14 h reaction time. However, when the excess alcohol was replaced by dimethyl sulfoxide, the yield of ether rose to 95% with 9.5 h reaction time. Other primary alkyl chlorides exhibited similar behavior to n-butyl chloride, but secondary alkyl chlorides and primary alkyl bromides gave little etherification, elimination being the major reaction. Unreactive halides, such as vinyl chloride, phenyl bromide, and 2,4-dinitrobromobenzene, were not etherified in dimethyl sulfoxide. The reaction products obtained from aliphatic dichlorides depended upon the relative positions of the chlorine atoms. Secondary alcohols reacted to give ethers, but tertiary alcohols were very unreactive. Polyols generally gave high yields of ethers, the major product being that in which all but one of the hydroxyl groups became etherified. Under forcing conditions, however, completely etherified polyols could be obtained.

Williamson Ether Synthesis on Solid Support:  Substitution versus Elimination

2001 ◽  
Vol 3 (2) ◽  
pp. 154-156 ◽  
Author(s):  
Avi Weissberg ◽  
Adi Dahan ◽  
Moshe Portnoy
Keyword(s):  
Solid Support ◽  
Ether Synthesis ◽  
Williamson Ether Synthesis
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