Master Organic Chemistry Reaction Guide

Decarboxylation of beta-keto carboxylic acids

Description:  When carboxylic acids containing a carbonyl group two bonds away (“on the  β carbon”) are heated, carbon dioxide is lost.

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Real-World Examples

Org. Synth. 1927, 7, 40

DOI Link: 10.15227/orgsyn.007.0040

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Org. Synth. 1934, 14, 58

DOI Link: 10.15227/orgsyn.014.0058

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Org. Synth. 1941, 21, 99

DOI Link: 10.15227/orgsyn.021.0099

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Org. Synth. 1951, 31, 74

DOI Link: 10.15227/orgsyn.031.0074

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Org. Synth. 1950, 30, 81

DOI Link: 10.15227/orgsyn.030.0081

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Org. Synth. 1968, 48, 56

DOI Link: 10.15227/orgsyn.048.0056

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Org. Synth. 1965, 45, 25

DOI Link: 10.15227/orgsyn.045.0025

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Comments

Comment section

6 thoughts on “Decarboxylation of beta-keto carboxylic acids

  1. We are doing carboxylation of Potassium 2,5-dichlorophenolate at 35 Bar and 120 deg C. But often we are getting very less conversion and are not able to understand the mechanism for the low conversion. IS the reaction irreversible and what are the parameters to control this

    1. Yes, you’re forming a carbonate. You need to trap it somehow otherwise it will decarboxylate. But why are you doing this? Why not treat the phenolate with Boc2O or something and be done with it.

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