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20.2.4.2.2 Malonic Acid by Ozonolysis of α-Angelica Lactone

DOI: 10.1055/sos-SD-120-00173

Yang, Z.; Dong, K.Science of Synthesis Knowledge Updatesearly view.

Platform chemicals are small functional molecules that can be produced in a straightforward manner and high yield from renewable sources such as sugars or lignocellulose, and that can be applied in the synthesis of various other higher value-added products. α-Angelica lactone [5-methylfuran-2(3H)-one] is derived from the platform chemical levulinic acid, which is readily available from the hydrolysis of C6 sugars or the oxidation of furfural in good yield. Malonic acid (2) and its derivatives can be prepared in good to high yield by ozonolysis of α-angelica lactone (Scheme 2).[‌4‌] This operationally simple, mild, and atom-economic protocol represents a way to access these high-value intermediates in a 100% renewable approach. The only byproducts are acetic acid or acetates, which can be easily separated by distillation. A variety of solvents were proven to be effective, including alcohols and water.

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