Hydrochloric Acid → 5-Ethyl-2-(ethylsulfanyl)phenol

Participants

Reaction Steps

To freshly distilled 3-ethylphenol (100 grams, 0.82 moles), was added aluminum turnings (1.62 grams, 0.06 moles) and the mixture was heated at 175° to 195° C. until hydrogen evolution had ceased. Ethyldisulfide (63 grams, 0.515 moles) was then added in one portion at 150° C. This mixture was then heated at 175° to 180° C. for 18 hours and then for about 7 hours at 196° C. The resulting mixture was hydrolyzed with 3 N HCl, extracted with diethylether, washed with water and dried over magnesium sulfate. Distillation of the mixture followed by a redistillation through a packed column gave, after removal of by-products and starting materials, 8.15 grams of 2-ethylthio-5-ethylphenol as verified by 1H and 13C NMR.

Provenance & Evidence