Methanol → 3,5-Dimethyl-4-hydroxybenzaldehyde

Participants

Reaction Steps

A mixture of 13.622 g(100 mmol) of mesitol, 285 mg (1.26 mmol) of neocuproine hydrate, 503 mg (5.0 mmol) of CuCl and 120 mL of methanol was stirred at ambient temperature for 9 hours under an oxygen blanket. The reaction mixture was then diluted with ethyl acetate and filtered. The methanol was stripped off and the residue diluted with additional ethyl acetate. The solution was washed twice with a 1% solution of ethylenediaminetetraacetic acid trisodium salt (EDTA-Na3.2H2O), water and brine, dried over MgSO4 and concentrated. There was obtained 13.92 g of an orange-gold solid which was shown by 1H NMR and GC to contain 11.88 g (79.2% yield) of 3,5-dimethyl-4-hydroxybenzaldehyde (DMHB).

Provenance & Evidence