Acetovanillone-d3 synthesis

Yield:80404-23-5 22%

Reaction Conditions:

with hydrogen;palladium on carbon in methanol;ethyl acetate; under 3000.3 Torr; for 2 h;

Steps:

1

Synthesis of 1-(4-hydroxy-(3-methoxy-d3)phenyl)ethanone (26). A mixture of 25 (14 g, 56 mmol)) and 20% Pd-C (700 mg, 5 wt %) in methanol (20 mL) and ethyl acetate (20 mL) was hydrogenated at 4 Bar H₂ for 2 hr. The mixture was filtered through a pad of Celite, washing the pad with ethyl acetate (200 mL). The filtrate solution was concentrated under reduced pressure and the crude product purified by column chromatography using 0-100% ethyl acetate/heptanes to give 2 g (22%) of 26. ¹H NMR (CDCl₃) δ: 7.56 (m, 2H), 6.96 (d, 1H), 6.06 (s, 1H), 2.57 (s, 3H). LCMS m/z=170.1 (M+H).

References:

US2008/255194,2008,A1 Location in patent:Page/Page column 12