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

Don't let static charges disrupt your weighing accuracy

Daily Sensitivity Test

Recognize and detect the effects of electrostatic charges on your balance

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