Acetic Acid → 2-Amino-4-chloro-5-methylphenol

Beteiligte Stoffe

Reaktionsschritte

To 15 ml of a solvent mixture of water-ethanol (1:1 (v:v)), there was added 0.5 ml of glacial acetic acid and heated under reflux. To the obtained solution, there were added 0.86 g of iron powder and 0.80 g (4.3 mmol) of 4-chloro-5-methyl-2-nitrophenol and the mixture was heated under reflux for additional 20 minutes. After cooling and adding 30 ml of acetone, the iron powder was filtered and washed with 50 ml of acetone. The filtrate was combined with the washing liquor and the solvent was distilled off therefrom under reduced pressure to thereby give a brown solid. The obtained product was subjected to silica gel column chromatography (Si60 manufactured by Merck; 230-400 mesh; 200 g; eluent: hexane-ethyl acetate (2:1 (v:v)). The solvent was distilled off from the 1,100-2,000 ml fraction and thus 0.29 g (1.8 mmol) of 2-amino-4-chloro-5-methylphenol was obtained as yellow crystals. The yield was 43%.

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