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 reaction was discovered by Karl Ludwig Reimer and Ferdinand Tiemann. In the simplest case, the product is salicylaldehyde:
[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-position of the phenate (5) to give dichloromethyl substituted phenol (7). After basic hydrolysis, the desired product (9) is formed.
[edit] References
- ^ Reimer, K.; Tiemann, F. Ber. 1876, 9, 824 & 1268 & 1285.
- ^ Wynberg, H. Chem. Rev. 1960, 60, 169. (Review)
- ^ Wynberg, H.; Meijer, E. W. Org. React. 1982, 28, 2. (Review)
- ^ Wynberg, H. Comp. Org. Syn. 1991, 2, 769-775. (Review)
