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Reimer-Tiemann reaction



The Reimer-Tiemann reaction is a chemical reaction used for the ortho-formylation of phenols.[1][2][3][4]

Additional recommended knowledge

Reaction mechanism

Chloroform (1) reacts with strong base to form the chloroform carbanion (2), which will quickly alpha-eliminate to give dichlorocarbene (3). Dichlorocarbene will react in the ortho- and para- position of the phenate (5) to give the dichloromethyl substituted phenol (7). After basic hydrolysis, the desired product (9) is formed.

References

  1. ^  Reimer, K.; Tiemann, F. Ber. 1876, 9, 824 & 1268 & 1285.
  2. ^  Wynberg, H. Chem. Rev. 1960, 60, 169. (Review)
  3. ^  Wynberg, H.; Meijer, E. W. Org. React. 1982, 28, 2. (Review)
  4. ^  Wynberg, H. Comp. Org. Syn. 1991, 2, 769-775. (Review)
  5. Russell, A.; Lockhart, L. B. Organic Syntheses, Coll. Vol. 3, p.463 (1955); Vol. 22, p.63 (1942). (Article)

See also

 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Reimer-Tiemann_reaction". A list of authors is available in Wikipedia.
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