Sulfuric Acid → 1-Hydroxy-3-(2,4,6-trichloro-phenyl)-propan-2-one

Participants

Reaction Conditions

Reaction Steps

To an emulsion of dodecylsulfanyl-3-(2,4,6-trichloro-phenyl)-prop-2-en-1-ol (0.82 g; 1.9 mmol), prepared as described in example P61 in methanol (3 ml) was added dropwise 30% sulfuric acid (1.5 ml; 5.6 mmol). The temperature increased from 23° C. until 28° C. The mixture was heated at 60° C. for 5 h. Dioxane (2 ml) was added and reaction was stirred at 60° C. for 18 h. The biphasic mixture was transferred in a sealed microwave vial and heated at 80° C. for 10 min and at 100° C. for 10 min. The mixture obtained was poured in water and was extracted once with ethyl acetate. Organic layer was washed three times with water, dried over sodium sulfate and evaporated. The crude oil obtained was subject to flash chromatography (eluant: c-hexane/ethyl acetate 4:1). 80 mg (18% of theory) of 1-hydroxy-3-(2,4,6-trichloro-phenyl)-propan-2-one was obtained as a light yellow solid.

Provenance & Evidence