Methyl 4-[7-formylnaphth-1-ylmethyl]-3-methoxybenzoate → Methyl 4-(7-carboxynaphth-1-ylmethyl)-3-methoxybenzoate

関与物質

反応手順

A solution of Jones reagent (1.53 ml) [prepared from 26.72 g chromium trioxide in 23 ml concentrated sulfuric acid, diluted with water to 100 ml] was added to a solution of methyl 4-(7-formylnaphth-1-yl-methyl)-3-methoxybenzoate (409 mg) in dimethylformamide (12 ml, distilled over CaH2). The mixture was stirred for 1 h and was partitioned between methylene chloride and 1N HCl. The organic layer was washed (1N HCl (twice), brine), dried (MgSO4) and evaporated. The residue was triturated with ether, ground to a powder and vacuum dried at 120° C. for 12 h to afford methyl 4-(7-carboxynaphth-1-ylmethyl)-3-methoxybenzoate (347 mg, 81%) as a pale yellow solid; mp 229.0°-230° C.; MS(CI), m/e=351(M+H).

情報源と証拠