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

Participants

Reaction Steps

Methyl 4-(4-hydroxy-1-butynyl)phenylacetate (10.6 g, 0.0485 mol) was dissolved in methanol (200 mL), then 10% palladium on carbon (1.1 g) was added, and the mixture was stirred under hydrogen (50 psi). After 6 hours, additional 10 % palladium on carbon (1 g) was added, and the mixture was stirred overnight. The catalyst was filtered through celite, the filtrate was concentrated and dried in vacuo to give 10.20 g (94.5%) of methyl 4-(4-hydroxy-1-butyl)phenylacetate as a yellow liquid. FAB-MS m/z=223 (M+H); HRMS calcd for C13H19O3 (M+H) 15 223.1334, found 223.1328.

Provenance & Evidence