19 Mar Reaction of phenol with chloroform and KOH to give salicylaldehyde is known as Reimer-Tiemann reaction. Mechanism:—- In this reaction,chloroform reacts first. The Reimer-Tiemann Reaction. Hans Wynberg. Chem. Rev., , 60 (2), pp – DOI: /cra Publication Date: April ACS Legacy . In the Reimer-Tiemann reaction a phenol is con- verted to an aromatic hydroxyaldehyde by warming with chloroform andaqueous alkali. CHCla. 10% NaOH.

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The direct formylation of aromatic compounds can be accomplished by various methods reatcion as the Gattermann reactionGattermann—Koch reactionVilsmeier—Haack reactionor Duff reaction ; however, in terms of ease and safety of operations, the Reimer—Tiemann reimer tiemann reaction is often the most advantageous route chosen in chemical synthesis.

This interaction favors selective ortho-forymation. The negative charge is delocalised into the aromatic ring, making it far more nucleophilic.

Reimer-Tiemann reaction

The Reimer—Tiemann reaction is effective for other hydroxy-aromatic compounds, such as naphthols. Berichte der deutschen chemischen Gesellschaft.

Nucleophilic attack of the dichlorocarbene reimer tiemann reaction an intermediate dichloromethyl substituted phenol 7. As such the Reimer-Tiemann reaction reimer tiemann reaction be unsuitable for substrates bearing these functional groups. Karl Reimer Reactjon Tiemann.


By virtue of its 2 electron-withdrawing chlorine groups, carbine 3 is highly electron deficient and is attracted to the electron rich tiemmann 5. Chloroform 1 is deprotonated rfaction a strong base normally hydroxide to form the chloroform carbanion 2 which will quickly alpha-eliminate to give dichlorocarbene 3 ; this is the principal reactive species. Organic Reactions, Volume From Wikipedia, the free encyclopedia.

After basic hydrolysis, the desired product 9 is formed. The two reagents reimer tiemann reaction therefore separated and must be brought together for the reaction to take place.

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Reimer–Tiemann reaction – Wikipedia

The Reimer—Tiemann reaction can be altered to yield phenolic acids rei,er reimer tiemann reaction the chloroform with carbon tetrachloride. In addition, many compounds can not withstand being heated in the presence of hydroxide.

This reimer tiemann reaction was last edited on 27 Juneat Dichlorocarbenes can react with alkenes and amines to respectively form dichlorocyclopropanes and isocyanides. Journal of the American Chemical Society.

FAQs on Reimer Tiemann Reaction in JEE

The reaction typically needs to be heated reimer tiemann reaction initiate reimer tiemann reaction process, however once started the Reimer-Tiemann Reaction can be highly exothermic; this combination makes it prone to thermal runaways.


Giemann can be achieved by rapid mixing, phase-transfer catalystsor an emulsifying agent the use of 1,4-Dioxane as a solvent is an example.

Berichte der deutschen chemischen Gesellschaft in German.

Tiemannn are not readily soluble in the chloroform, thus the reaction is generally carried out reimer tiemann reaction a biphasic solvent system.

In the simplest sense this consists of an aqueous hydroxide solution and an organic phase containing the chloroform. Substitution reactions Addition reactions Carbon-carbon bond forming reactions Name reactions Formylation reactions.

The Reimer—Tiemann reaction is a chemical reaction reimer tiemann reaction for the ortho – formylation of phenols ; [1] [2] [3] [4] reimmer with the simplest example being the conversion of phenol to salicylaldehyde. The hydroxide will also deprotonate the phenol 4 to give a negatively charged phenoxide 5. By using this site, you agree to the Terms of Use and Privacy Policy.