tert-Butyl methyl ether → Ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoate

Participants

Reaction Steps

Ethyl E/Z-3-(4-benzyloxyphenyl)-2-ethoxyacrylate (20.0 g, 61.3 mmol) dissolved in tert-butyl methyl ether (40 mL) charged with palladium on carbon (5%) (1.0 g, Engelhard Tech code no. 4531) was hydrogenated with vigorous stirring at atmospheric pressure at room temperature for 2-3 days. The catalyst was filtered off and washed with a few milliliters of tent-butyl methyl ether. The combined filtrates were concentrated in vacuo to yield 14.5 g (99% yield) of the title compound as a viscous oil, which crystallizes upon standin.

Provenance & Evidence