Practical large scale synthesis of half-esters of malonic acid.
A practical large-scale synthesis of monomethyl malonate and monoethyl malonate, which are among the most commonly applied half-esters in organic synthesis, is described, applying the highly efficient selective monohydrolysis of symmetric diesters we reported before. The optimal conditions with regard to the type of base, equivalent, co-solvents, and the reaction time have been examined for large-scale reactions. Monomethyl malonate and monoethyl malonate were obtained in high yields with near 100% purity within only half a day. The conditions of this selective monohydrolysis reaction are environmentally benign and straightforward, as it requires only water, a small proportion of a volatile co-solvent, and inexpensive reagents, and produces no hazardous by-products, and therefore the synthetic utility of this reaction in process chemistry is expected.
Niwayama
Satomi
S
Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409-1061, USA. satomi.niwayama@ttu.edu
Cho
Hanjoung
H
D004952:Esters / Q000737:chemistry; D008314:Malonates / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
D004952:Esters; D008314:Malonates; C540852:monoethyl malonate; C540851:monomethyl malonate; C030290:malonic acid