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

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

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 with Phenols at a Tertiary Stereogenic Carbon: Formal Enantioselective Phenoxylation of β‐Keto Esters

2015 ◽  
Vol 21 (40) ◽  
pp. 14095-14098 ◽  
Author(s):  
Kazutaka Shibatomi ◽  
Manato Kotozaki ◽  
Nozomi Sasaki ◽  
Ikuhide Fujisawa ◽  
Seiji Iwasa
Keyword(s):  
Keto Esters ◽  
Ether Synthesis ◽  
Williamson Ether Synthesis

scholarly journals Versatile Synthetic Route for Resveratrol Modification via Amine Functionalization

2019 ◽  
Vol 14 (9) ◽  
pp. 1934578X1987621
Author(s):  
Masayoshi Yanagi ◽  
Noriyuki Uchida ◽  
Hiroki Hamada
Keyword(s):  
Rhodamine B ◽  
Trifluoroacetic Acid ◽  
Primary Amine ◽  
Functional Group ◽  
Amine Group ◽  
Amine Functionalization ◽  
Synthetic Route ◽  
Amine Functional Group ◽  
Ether Synthesis ◽  
Williamson Ether Synthesis

Resveratrol derivatives containing a primary amine functional group were synthesized by an introduction of N-Boc-bromoethylamine to resveratrol using Williamson ether synthesis and subsequent deprotection of the Boc group with trifluoroacetic acid. After conjugation of fluorescent NBD-F or rhodamine B with isothiocyanate (Rhd B-ITC) using the amine group, resveratrols modified with NBD or Rhd B (Resveratrol-NBD and Resveratrol-Rhd B, respectively) were successfully obtained.

Formation of Molecular Monolayers on TiO2Surfaces: A Surface Analogue of the Williamson Ether Synthesis

Langmuir ◽  
2011 ◽  
Vol 27 (11) ◽  
pp. 6879-6889 ◽  
Author(s):  
Jixin Chen ◽  
Ryan Franking ◽  
Rose E. Ruther ◽  
Yizheng Tan ◽  
Xueying He ◽  
...  
Keyword(s):  
Molecular Monolayers ◽  
Ether Synthesis ◽  
Williamson Ether Synthesis

ChemInform Abstract: Potassium Hydride in Paraffin: A Useful Base for Williamson Ether Synthesis.

ChemInform ◽  
2010 ◽  
Vol 41 (39) ◽  
pp. no-no
Author(s):  
Haihong Huang ◽  
Christopher G. Nelson ◽  
Douglass F. Taber
Keyword(s):  
Ether Synthesis ◽  
Potassium Hydride ◽  
Williamson Ether Synthesis
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