1-Naphthalenemethanol → 1-Naphthaldehyde

Participants

Reaction Steps

1-naphthylmethanol (500 mg, 3.2 mmol) in 2 g tributylphosphate was allowed to react with electrochemically produced Co(III) sulphate at 24° C. in the cell of FIG. 1 but having a U-tube format, i.e. lacking the crank 23. (This cell was also used in the following reactions, unless otherwise stated.) The electrolyte solution was composed of 0.12M Co(II) sulphate in 2M H2SO4. After 27 hours at 200 mA, no starting material remained as shown by thin-layer chromatography. The organic material isolated from this run was placed on a silica gel column, which was eluted with a 20% ether in petroleum ether (bp=60°-80° C.) solution. The initial band gave 326 mg (2.09 mmol, 66%) of 1-naphthaldehyde. A second band gave 14 mg (0.08 mmol, 2%) of a yellow solid which was identified as 1-naphthoic acid by its infrared spectrum and mass spectrum. After recrystallization from ether-petroleum ether, colourless needles were obtained that had a melting point of 158°-162° C. (authentic sample mp=158°-162° C.).

Provenance & Evidence