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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R1 = alkyl group L = leaving team

The group —CH2CO2H in 2 is added by a malonic ester, thus the term malonic ester synthesis.

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reaction 1:

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reaction 2:

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reaction 3:

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reaction 4:

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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.

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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.

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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:

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reaction 1:

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reaction 2:

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reaction 1 (repeat):

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reaction 2 (repeat):

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reaction 3:

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reaction 4:

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Malonic Ester Synthesis

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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.

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Because Sodio Malonic Ester is an enolate, it can then be alkylated v alkyl halides.

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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.