Reimer-Tiemann reaction

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

The Reimer-Tiemann reaction

[edit] 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.

The mechanism of the Reimer-Tiemann reaction

[edit] 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)

[edit] See also

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