Methanol → HCID 131716725, compound

Participants

Reaction Steps

Methyl acrylate (820.67 g., 9.5327 mol) was added, over 100 min, under N2, to a magnetically stirred solution of methyl thioglycolate (1007.18 g, 9.489 mol) and triethylamine (138.96 g, 192 mL, 1.373 mol) in methanol (1000 mL, plus a subsequent 239.83 g from a wash-bottle, for rinsings). After the reaction vessel became warm, the reaction vessel (a 4L heavy-wall Erlenmeyer flask) was immersed in a bucket of cold water to moderate the reaction. The reaction mixture was permitted to stand overnight and was then concentrated on a rotary evaporator. The residue was distilled in vacuo in two lots (bp 122°-131° C./1.5 torr) to yield 1804.37 g (98.9%). NMR and GC/MS data agreed with the proposed structure, which is a known compound (see R. B. Woodward and R. H. Eastman, J. Am. Chem. Soc., 68, 2229-2235 (1946)).

Provenance & Evidence