Acetone → 2-(2,4,6-Trimethylphenyl)propan-2-ol

Participants

Reaction Conditions

Reaction Steps

According to Example 3, mesitylmagnesium bromide (1.20 M in THF; 1.83 mL; 2.20 mmol; 1.10 equiv) was placed in a flame dried schlenk flask under an argon atmosphere and cooled to 0° C. At this temperature, LaCl3.2LiCl (0.33 M; 6.06 mL, 2.00 mmol, 1.00 equiv) was slowly added. The resulting mixture was allowed to warm up to room temperature and stirred for 4 h. Then, after cooling to 0° C., acetone (116 mg; 2.00 mmol) was added and the reaction was warmed up to room temperature and stirred for another hour at this temperature. When the end of the reaction was reached (GC-monitoring of aliquots), sat. aq. NH4Cl (2 mL) and water (2 mL) were added. The aqueous layer was extracted with ether (4×10 mL), the combined extracts were dried (Na2SO4) and evaporated in vacuo. Column chromatographical purification (silica; pentane:Et2O 9:1) afforded the desired product as colorless, crystalline solid, mp=106−107° C. (245 mg, 69%).

Provenance & Evidence