[CH3:1][Mg]Br.COC(=O)[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[CH:9]=1.C([O:19][CH2:20][CH3:21])(=O)C.Cl>O1CCCC1.O>[OH:14][C:10]([CH3:11])([CH3:1])[CH2:9][C:8]1[CH:7]=[C:20]([OH:19])[CH:21]=[CH:12][CH:13]=1
To a solution of methyl magnesium bromide (3 M, 12 mL, 36.06 mmol) cooled to 0° C. was added tetrahydrofuran (10 mL) and (3-hydroxy-phenyl)-acetic acid methyl ester (1 g, 6.01 mmol) as a solution in tetrahydrofuran (5 mL). The resulting mixture was warmed to room temperature stirred for 30 min and then poured carefully into a biphasic mixture of ethyl acetate and water. The water layer was made acidic (pH=1) with 1N aqueous hydrochloric acid and extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo which afforded 3-(2-hydroxy-2-methyl-propyl)-phenol (1 g, 100%) as a white solid.
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