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Chem 343 – Organic Reactions Chapter 10 Prepared by José Laboy, MS http://www.chem.wisc.edu/areas/clc (Resource page) Reactions of Alcohols #4: Ethers from Alcohols Using Sulfonates Mechanism OH
1) NaH or NaOH
2) (CH3)2SO4
O
H
O
H
OCH3
H3C
O
S
O
CH3
OCH3
O
O
O
dimethylsulfonate
SN2 Reaction
The synthesis is very useful in preparing methyl esthers. +
O
S
O
O
CH3
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