methyl 4-(4-hydroxy-1-butynyl)phenylacetate → methyl 4-(4-hydroxybutyl)phenylacetate

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Reaction Steps

A solution of methyl 4-(4-hydroxybutyn-1-yl)phenylacetate (178 mg, 0.82 mmole) and 10% palladium on carbon (30 mg) in ethanol (2 mL) were stirred under a balloon of hydrogen for 3 days at room temperature. The mixture was filtered and the filtrate concentrated in vacuo to give the title compound (181 mg) as an oil. NMR (CDCl3): δ 1.52 (s, 1H); 1.64 (m, 2H); 1.71 (m, 2H); 2.65 (t, 2H); 3.61 (s, 2H); 3.68 (t, 2H); 3.71 (s, 3H); 7.15 (d, 2H); 7.21 (d, 2H).

Provenance & Evidence