C[Mg]Br.C([O:6][CH2:7][CH3:8])C.[OH:9][C:10]1[C:17]([CH:18]([CH3:20])[CH3:19])=[CH:16][C:15]([CH:21]([CH3:23])[CH3:22])=[CH:14][C:11]=1C#N.Cl>O.C1COCC1>[OH:9][C:10]1[C:17]([CH:18]([CH3:19])[CH3:20])=[CH:16][C:15]([CH:21]([CH3:23])[CH3:22])=[CH:14][C:11]=1[C:7](=[O:6])[CH3:8]
To dry THF (10 mL) there was added 3.0 M solution of methylmagnesium bromide in diethylether (Aldrich) (10.9 mL; 32.8 mmole) and then a previously prepared solution of 2-hydroxy-3,5-diisopropyl benzonitrile (2.78 g, 13.7 mmole) and dry THF (70 mL) was added. After 7 hours under the reflux the reaction mixture was mixed with water (100 mL), acidified with concentrated hydrochloric acid (50 mL) and refluxed for one more hour. After cooling and extraction with ethyl acetate an oily product was obtained, which was purified on a silica gel column, whereat there were obtained 380 mg (12.5%) of 2′-hydroxy-3′5′-diisopropylacetophenone:
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