Reimer-Tiemann reaction

Reimer-Tiemann reaction

The Reimer-Tiemann reaction is a chemical reaction used for the ortho-formylation of phenols.Ref|Reimer1876Ref|Wynberg1960Ref|Wynberg1982Ref|Wynberg1991 The reaction was discoverd by Karl Ludwig Reimer and Ferdinand Tiemann

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

# 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). ( [http://www.orgsyn.org/orgsyn/prep.asp?prep=cv3p0463 Article] )

See also

* Duff reaction
* Gattermann aldehyde synthesis


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