1,4-Naphthalenediol → 1,4-Naphthoquinone

Participants

Reaction Steps

1,4-Dihydroxynaphthalene (80 mg, 0.50 mmol) and bis-(p-methoxyphenyl)-telluroxide (196 mg, 0.55 mmol) were stirred in chloroform (4 ml) at room temperature under argon for 1 h. The reaction mixture was concentrated by evaporation of the solvent under reduced pressure and p.l.c. (benzene-ethyl acetate 9:1) gave bis-(p-methoxyphenyl)-telluride (96 mg, 56%) and p-naphthoquinone (77 mg, 97%) as an olive green solid m.p. 122°-125° which on recrystallisation from ethanol gave yellow needles (60 mg, 76%) m.p. 125°-126° (lit., 126) δ(CDCl3) 8.27-7.67 (4H, m), and 7.00 (2H, S).

Provenance & Evidence