Malonic ester is a reagent specifically used in a reaction i m sorry converts alkyl halides to carboxylic acids dubbed the Malonic Ester Synthesis. Malonic ester synthetic is a fabricated procedure used to convert a compound that has actually the general structural formula 1 right into a carboxylic mountain that has actually the basic structural formula 2.
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The group —CH2CO2H in 2 is added by a malonic ester, thus the term malonic ester synthesis.
reaction 1:
reaction 2:
reaction 3:
reaction 4:
A an ext direct method to transform 3 right into 4 is the reaction of 3 with the enolate ion (5) that ethyl acetate followed by hydrolysis the the result ester.
However, the generation the 5 from ethyl acetate quantitatively in high yield is not an easy task due to the fact that the reaction requires a very solid base, such as LDA, and must be brought out at very low temperature under strict anhydrous conditions.
Malonic ester synthesis offers a more convenient alternate to convert 3 to 4.
Malonic ester synthesis can be adjusted to synthesize compound that have actually the basic structural formula 6.
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R3, R4 = identical or various alkyl groups
eg:
reaction 1:
reaction 2:
reaction 1 (repeat):
reaction 2 (repeat):
reaction 3:
reaction 4:
Malonic Ester Synthesis
Due to the fact that Malonic ester’s α hydrogens are nearby to two carbonyls, they can be deprotonated by sodium ethoxide (NaOEt) to form Sodio Malonic Ester.
Because Sodio Malonic Ester is an enolate, it can then be alkylated v alkyl halides.
After alkylation the product can be convert to a dicarboxylic acid with saponification and subsequently one of the carboxylic acids have the right to be removed through a decarboxylation step.