Succinic acid from malonic ester

The Brown-Walker 1 method has been found to be of excellent service in the electrolysis of the potassium salts of the mono-esters of malonie acid. The formation of the diethyl ester of succinic acid from ethyl potassium malonate has already been mentioned fp. 103). 

From Malonic Ester.—The same constitution is also proven by an interesting synthesis from malonic ester. Mono-sodium di-ethyl malonate reacts with monobrom, or mono-iodo acetic acid, and yields the ester of a tri-carboxy acid which after hydrolysis to the acid loses carbon di-oxide and yields succinic acid. 

Figure 1. Total ion current of n-butyl esters of the acidic fraction from non-sterile leaf washings of C. sativa. Key 1 = oxalic acid 2 = malonic acid 3 = maleic acid 4 = succinic acid 5 = fumaric acid 6 = alpha-ketoglutaric acid 7 = cis-aconitic acid 8 = citric acid (19)-...

Thus the diethyl ester of succinic acid is formed from ethyl potassium malonate ... 

The classical preparation of cyclobutyl ketones involves the base-catalyzed reaction of 1,3-dihaloalkanes with malonate esters. However, the initial product of this reaction is a cyclobutane carboxylic acid. S.D. Van Arnum and co-workers showed that cyclobutyl ketones can be efficiently synthesized starting from acyl succinates and using the... 

Fig. 3.10 Chromatogram of standard acids separated as their benzyl esters on a SE-30 column using temperature programming from 144°C to 257°C at 3°C min then 257°C to 290°C at 5°C min" and isothermal at 290°C. Peak identifications are 1, lactic acid 2, 3-hydroxybutyric acid 3, oxalic acid 4, malonic acid 5, pyruvic benzoxime 6, maleic acid 7, succinic acid 8, fumaric acid 9 glutaric acid 10, malic acid 11, adipic acid 12, 2-oxoglutaric benzoxime 13, oxaloacetic benzoxime. (Redrawn with modifications from Oehlenschlager et al., 1975)...

Glucose esters of 3-N. (endecaphyllins) are responsible for the toxicity of Indigofera endecaphylla for grazing animals. 3-N. functions as suicide substrate of succinate dehydrogenase where the formed 3-nitro-acrylic acid adds to the active thiol group of the enzyme. The compound is formed biosynthetically in Penicillium atrovenetum from L-aspartic acid which is oxidized to the a-nitrosuccinate and then decarboxy-lated to furnish the aci-nitro form of 3-N.. Malonate and N-hydroxymalonamate appear to be intermediates in Indigofera spicata. 

Fig. 3.2 Chromatogram of standard acids as their methyl esters, separated on a 3 ft (0.001 m i.d.) glass column packed with 5 per cent poly(ethylene glycol) adipate on silanized Gas Pack W (100-120 mesh) using temperature programming from 80°C to 180°C at 10°C min" with an initial isothermal delay of 1.33 min. Peak identifications are 1, lactate 2, pyruvate 3, malonate (internal standard) 4, fumarate 5, succinate 6, adipate (internal standard) 7, malate 8 and 9,2-oxoglutarate 10, cw-aconitate, 11, citrate 12, isocitrate. (Redrawn with modifications from De Silva, 1971)...

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