Acetic Acid → 6-Methoxy-3-methylbenzo[d]isoxazole-7-carbaldehyde

Participants

Reaction Steps

To a solution of commercially available 3-methylbenzo[d]isoxazol-6-ol (1.125 g; 7.54 mmol) in acetic acid (22.5 ml) was added hexamethylenetetramine (4.500 g; 32.09 mmol), and the resulting mixture was heated over a steam-bath for 6 h. The resulting hot mixture was then treated with 6 M aq. HCl (20 ml), and the heating was continued for 30 min. The solid obtained on dilution of the reaction mixture was filtered, and recrystallised from aq. MeOH to give the desired 6-hydroxy-3-methylbenzo[d]isoxazole-7-carbaldehyde as a yellow solid. LC-MS (conditions D): tR=0.79 min.; [M+H]+: 177.98 g/mol.

Provenance & Evidence