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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In addition, many compounds can not withstand being heated in the presence of hydroxide.

Nucleophilic attack of the dichlorocarbene gives an intermediate dichloromethyl substituted phenol 7. Organic Reactions, Volume The two reagents are therefore separated and must be brought together for the reaction to take place.

The Reimer—Tiemann reaction can be altered to yield phenolic reimer tiemann reaction by substituting the chloroform with carbon tetrachloride. Retrieved reimer tiemann reaction January This interaction favors selective ortho-forymation.

This page was last edited on 27 Juneat Views Read Edit View history. As such the Reimer-Tiemann reaction may be unsuitable for substrates bearing these functional groups.


chemistry world: Reimer–Tiemann reaction _ an electrophillic substitution or carbene attack.

Karl Reimer Ferdinand Tiemann. Berichte der deutschen chemischen Gesellschaft. By using this site, you agree to the Terms of Use and Privacy Policy. Chloroform 1 reactioon deprotonated by a strong base normally hydroxide to form the chloroform carbanion 2 which will quickly alpha-eliminate to give dichlorocarbene 3 ; this is the reimer tiemann reaction reactive species. By virtue of reimer tiemann reaction 2 electron-withdrawing chlorine groups, carbine 3 is highly electron deficient and is attracted to the electron rich phenoxide 5.

Reimer–Tiemann reaction

Dichlorocarbenes can react with alkenes and amines to respectively form dichlorocyclopropanes and isocyanides. The reaction typically needs to be heated to initiate the process, however once started the Reimer-Tiemann Reaction can be highly exothermic; this combination makes it prone to thermal runaways. Berichte der deutschen chemischen Gesellschaft in German.

Hydroxides are reimer tiemann reaction readily soluble in the chloroform, thus the reaction is generally carried out in a biphasic solvent system. The direct formylation of aromatic compounds can be accomplished by various methods such as reimer tiemann reaction Gattermann reactionGattermann—Koch reaction reimer tiemann reaction, Vilsmeier—Haack reactionor Duff reaction ; however, in terms of ease and safety of operations, the Reimer—Tiemann reaction is often the most advantageous route chosen in chemical synthesis.

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Journal of the American Chemical Society. From Wikipedia, the free encyclopedia. Substitution reactions Addition reactions Carbon-carbon bond forming reactions Name reactions Formylation reactions.

The hydroxide will also deprotonate the phenol 4 to remier a negatively charged phenoxide 5. The Reimer—Tiemann reaction is effective for other hydroxy-aromatic compounds, reimer tiemann reaction as naphthols.

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

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The negative charge is delocalised into the aromatic ring, making it far more nucleophilic. After basic hydrolysis, the desired product 9 is formed.

The Reimer—Tiemann reaction is a chemical reaction used rezction the ortho – formylation of phenols ; [1] [2] [3] [4] [5] with the simplest example being the conversion of phenol to salicylaldehyde. Retrieved from ” https: In the simplest sense this consists of an aqueous reimer tiemann reaction solution and an organic phase containing the chloroform.