Hydrochloric Acid → 3-Methyl-2-sulfanylphenol

Participants

Reaction Conditions

Reaction Steps

5.3 g (0.077 mol) of sodium nitrite in solution in 12 ml of water are added dropwise to a round-bottomed flask comprising 14 g of ice, 14 ml of 36% hydrochloric acid and 8.62 g (0.07 mol) of 2-amino-m-cresol. The mixture, kept at 0° C., is subsequently poured slowly into a solution of 15 g (0.093 mol) of potassium ethyl xanthate in 20 ml of water held at 40° C. The heating bath is removed and the mixture is stirred for 3 hours and then extracted with ethyl ether. The combined organic phases are washed with aqueous saline solution, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue is purified by fast chromatography on silica gel (eluent: cyclohexane/dichloromethane=65:35). The oil obtained is taken up in 20 ml of ethanol and the mixture is heated to 100° C. 20 ml of an ethanolic potassium hydroxide solution (7N) are then added dropwise. After 4 hours at 100° C., the mixture is cooled, concentrated under reduced pressure, acidified using hydrochloric acid (2N) and then extracted with ethyl ether. The combined organic phases are dried over magnesium sulfate, filtered and concentrated under reduced pressure to give a yellow oil which is not isolated but is used directly in the following stage.

Provenance & Evidence