1576. n-Butylmalonic Acid

Nomenclature

CAS number: 534-59-8
2-Butylpropanedioic acid; pentane-1,1-dicarboxylic acid.
C7H12O4; mol wt 160.17.
C 52.49%, H 7.55%, O 39.96%.

Description and references

Prepd by the interaction of sodium n-amyl chloride and carbon dioxide under pressure with ligroin as solvent: Morton et al., J. Am. Chem. Soc. 58, 754 (1936).

Chemical structure

Properties

Prisms from water, mp 102°. pK (5°): 2.96. Sol in water: 100 g of a satd aq soln contain 11.6 g at 0°; 79.3 g at 50°. Sol in alc, ether. Heating to 150° yields caproic acid.

Derivative

Diethyl ester.

Nomenclature

CAS number: 133-08-4
C11H20O4; mol wt 216.27.
C 61.09%, H 9.32%, O 29.59%.

Properties

Prepared by the interaction of n-butyl bromide, diethyl malonate, and sodium alcoholate: Adams, Kamm, Org. Synth. 4, 11 (1925). Liquid, bp760 235-240°; bp40 140-145°; bp20 130-135°. nD20 1.425. Very sol in alcohol, ether.