C[Mg]Br.[NH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11](=[O:13])[CH3:12].Cl.[C:15](=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.C1COCC1>[NH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]([CH3:15])([CH3:12])[OH:13]To a 0° C. solution of methylmagnesium bromide (45 mL of a 1.4M solution in toluene, 63 mmol) under nitrogen atmosphere was added a solution of ortho-aminoacetophenone (2.9 g, 21.5 mmol) in THF (20 mL). The mixture was warmed to ambient temperature for 45 min, cooled to 0° C., and poured into ice-water. The mixture was acidified with 6N HCl, adjusted to ca. pH 6 with saturated sodium bicarbonate solution, and then extracted with ether (2×100 mL). The combined ether fractions were dried (MgSO4), filtered and the solvent was removed under reduced pressure to give the oily product, 2-aminophenyldimethyl carbinol.
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