Williamson ether synthesis

Williamson Ether Synthesis
Named after Alexander William Williamson
Reaction type Coupling reaction
Identifiers
Organic Chemistry Portal williamson-synthesis
RSC ontology ID RXNO:0000090
Ether synthesis by reaction of salicylaldehyde with chloroacetic acid and sodium hydroxide[1]

The Williamson ether synthesis is an organic reaction, forming an ether from an organohalide and a deprotonated alcohol (alkoxide). This reaction was developed by Alexander Williamson in 1850.[2] Typically it involves the reaction of an alkoxide ion with a primary alkyl halide via an SN2 reaction. This reaction is important in the history of organic chemistry because it helped prove the structure of ethers.

The general reaction mechanism is as follows:[3]

Williamson ether synthesis mechanism

An example is the reaction of sodium ethoxide with chloroethane to form diethyl ether and sodium chloride:

  1. ^ Burgstahler, Albert W.; Worden, Leonard R. (1966). "Coumarone". Organic Syntheses. 46: 28. doi:10.15227/orgsyn.046.0028; Collected Volumes, vol. 5, p. 251.
  2. ^ Williamson, Alexander (1850). "Theory of Ætherification". Philosophical Magazine. 37 (251): 350–356. doi:10.1080/14786445008646627. (Link to excerpt.)
  3. ^ Boyd, Robert Neilson; Morrison, Robert Thornton (1992). Organic Chemistry (6th ed.). Englewood Cliffs, N.J.: Prentice Hall. pp. 241–242. ISBN 9780136436690.