Synthesis of Ethers ROR

Ethers are frequently prepared via the Williamson ether synthesis, which involves the reaction of an alkyl halide electrophile (RX) with an alkoxide nucleophile (R O ). As usual, the Sn2 backside attack is sensitive to sterics, and the E2 elimination reaction is expected to compete here since alkoxides are strong bases. The Sn2 substitution can be expected to give good yields of the ether if the halide is on a methyl, primary, allylic, or benzylic carbon. Simple alkoxides may be commercially available otherwise, the alkoxide can be prepared from the corresponding alcohol by treatment with a strong base (NaH) or a metal (Na or K). 

Introduction to Strategies for Organic Synthesis, First Edition. Laurie S. Starkey. 2012 John Wiley Sons, Inc. Published 2012 by John Wiley Sons, Inc. 

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