Williamson ether synthesis

Schematic of the Williamson ether synthesis. Reagents: alcohol, base, alkyl halide. Product: ether.

The Williamson ether synthesis is an organic reaction used to convert an alcohol and an alkyl halide to an ether using a base such as NaOH. The mechanism begins with the base abstracting the proton from the alcohol to form an alkoxide intermediate. The alkoxide then attacks the alkyl halide in a nucleophilic substi-tution reaction (SN2), which results in the formation of the final ether product and a metal halide by-product.[1][2]

Mechanism

Mechanism of the Williamson ether synthesis. SN2 attack.

References:

1.
Williamson, A. Ann. Chem. Pharm. 1851, 77, 37–49.
2.
Williamson, A. W. Q. J. Chem. Soc. 1852, 4, 229