Reimer-Tiemann reaction

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

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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

• Duff reaction
• Gattermann aldehyde synthesis