Etherificasion
Williamson ether synthesis of 2-octadecyloxynaphthalene
2.10.2014
J Patrick N Yap, s2667398 j.yap.1@student.rug.nl
Abstract
In this experiment is an organic reaction, forming ether from alcohol. Alexander Williamson discovered this reaction in 1850. Usually suitable either on the basis of availability or reactivity. The Williamson reaction is also frequently used to prepare an ether indirectly from two alcohols. One of the alcohols is first converted to a leaving group, then other two reacted. Alkyl is treated with alkoxide ion. Alkoxide can easily formed by doing alcohol with base.
Theory
2-octadecyloxynaphthalene made by SN2 reaction, by carbon from BrC18H27 attacked by alkoxide of alcohol and substitute Br. The alcohol first being deprotonated (2-napthol). And then continue to SN2 reaction wich the negative charge from alkoxide attack on the positive charge carbon on BrC18H27.
Experimental
0,5 g of 2-napthol and 25ml acetonitrile were stirred with 1,234 g of Cesium carbonate and 1-bromooctadecane on three necked flask that was placed on magnetic trirrer adn reflux condenser. Around 11.17 the mixture start heated at 23०C. While the temperature rising up the color of the mixture changed to dark color green, reflux happen at 11.32 water droping back to the three necked flask. The compounds in the mixture checked by TLC ( Thin Layer Chromatography). After three attempt of the TLC, founded that there are 0,86cm for Rf calue of the compounds.
The mixture were cooled down and transfer the mixture to 250ml round bottom flask. After that 150ml of diethyl were add and washing phase start by the mixture being poured into the separatory funnel. the mixture then being shaken firmly and the layer were made. the lower layer being removed and the ether layer stay. 1 spoon of MgSO4 were added and filtered after move the mixture to an erlenmeyer. the solvent then being evaporated and removed. Due to the limited of
2.10.2014
J Patrick N Yap, s2667398 j.yap.1@student.rug.nl
Abstract
In this experiment is an organic reaction, forming ether from alcohol. Alexander Williamson discovered this reaction in 1850. Usually suitable either on the basis of availability or reactivity. The Williamson reaction is also frequently used to prepare an ether indirectly from two alcohols. One of the alcohols is first converted to a leaving group, then other two reacted. Alkyl is treated with alkoxide ion. Alkoxide can easily formed by doing alcohol with base.
Theory
2-octadecyloxynaphthalene made by SN2 reaction, by carbon from BrC18H27 attacked by alkoxide of alcohol and substitute Br. The alcohol first being deprotonated (2-napthol). And then continue to SN2 reaction wich the negative charge from alkoxide attack on the positive charge carbon on BrC18H27.
Experimental
0,5 g of 2-napthol and 25ml acetonitrile were stirred with 1,234 g of Cesium carbonate and 1-bromooctadecane on three necked flask that was placed on magnetic trirrer adn reflux condenser. Around 11.17 the mixture start heated at 23०C. While the temperature rising up the color of the mixture changed to dark color green, reflux happen at 11.32 water droping back to the three necked flask. The compounds in the mixture checked by TLC ( Thin Layer Chromatography). After three attempt of the TLC, founded that there are 0,86cm for Rf calue of the compounds.
The mixture were cooled down and transfer the mixture to 250ml round bottom flask. After that 150ml of diethyl were add and washing phase start by the mixture being poured into the separatory funnel. the mixture then being shaken firmly and the layer were made. the lower layer being removed and the ether layer stay. 1 spoon of MgSO4 were added and filtered after move the mixture to an erlenmeyer. the solvent then being evaporated and removed. Due to the limited of
Bibliography: http://en.wikipedia.org http://www.webqc.org