The Reimer-Tiemann reaction
is a chemical reaction
used for the ortho-formylation
. The reaction was discoverd by Karl Ludwig Reimer
and Ferdinand Tiemann
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.
- 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)
- Russell, A.; Lockhart, L. B. Organic Syntheses, Coll. Vol. 3, p.463 (1955); Vol. 22, p.63 (1942). (Article)