1-(2,5-Dimethoxyphenyl)prop-2-en-1-ol → 2,5-Dimethoxyphenyl vinyl ketone

Participants

Reaction Steps

Activated MnO2 (100 g) was added in portions to a mechanically stirred solution of 2,5-dimethoxyphenyl vinyl carbinol (12.5 g, 0.064 mole) in 250 ml of methylene chloride. The mixture was stirred at room temperature for 24 hours and then filtered through a patch of Celite. The filtrate was concentrated to give a brown oil which was purified by column chromatography on silica gel, using diethyl ether/hexane (1/1) as eluant. The compound was obtained as a light brown oil; 7.2 g; IR (neat) 1680 cm-1 ; NMR (CDCl3) δ6.85-7.1 (m,4H); 6.3 (d,1H); 5.8 (d,1H); 3.8 and 3.85 (two singlets,6H).

Provenance & Evidence