Methyl Acrylate → 4-[(1E)-3-(Methyloxy)-3-oxo-1-propen-1-yl]-1-naphthalenecarboxylic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-bromo-1-naphthalenecarboxylic acid (9.42 g), triethylamine (25 ml), palladium acetate (0.85 g), triphenylphosphine (0.98 g) and methyl acrylate (9.68 g) in anhydrous DMF (95 ml) was heated to 100° C. for 1 h under nitrogen. The mixture was allowed to cool to room temperature, filtered through Celite and washed with diethyl ether/water. The filtrate was extracted with ether, then with EtOAc. The aqueous phase was acidified to approximately pH 1 with 2 M aqueous hydrogen chloride. The solid was filtered, washed with water and dried at 40° C. under vacuum, to afford the title compound (8.2 g).

Provenance & Evidence