Diethyl Ether → 2-(2-Amino-3-methylphenyl)propan-2-ol

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Reaction Steps

130 ml of a 3 M solution of methyl magnesium chloride in 130 ml of THF was added drop-by-drop to a stirred solution of 11 g of 49A in 70 ml of dry ether at 0°-5° C. in a nitrogen atmosphere. The resulting mixture was allowed to warm to room temperature and stirred at reflux (40° C.) for 5 hours and held overnight at room temperature. The mixture then was quenched in a mixture of 48 g of ammonium chloride and 350 g of ice. 30 ml of 3 N hydrochloric acid was added, the solvents were evaporated, and the residue was extracted with ether. The extract phase was washed with water, then brine, dried (K2CO3), filtered and stripped of solvent. The residue was recrystallized from hexane to give (2-amino-3-methylphenyl)dimethylcarbinol (49B), as colorless needles, m.p.: 78°-79° C.

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