Methyl Salicylate → HCID 57073919, compound

Participants

Reaction Conditions

Reaction Steps

To a one liter autoclave was added a mixture of 304 g. (2.0 moles) methyl salicylate (III), 4.0 g. triethylamine and 150 g. (2.1 mole) of 1,2-butylene oxide. The reaction mixture was heated under nitrogen at 150° C for 6 hours. The clear brown liquid crude reaction product (444 g.) was then removed from the autoclave and fractionally distilled (4489-84 and 4524-25) through a 3 ft. Vigreaux (Goodloe packed) column after addition of 2 g. sodium acetate to aid hydrolysis. Traces of glycol and catalyst (Et N) were removed at first, but the main fraction (4524-25), 160 g. was identified (NMR, IR) as the pure title compound IX. On standing in air IX solidified and could be recrystallized from cyclohexane as prisms, m.p. 63°-66° C.

Provenance & Evidence