[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH:7][C:8]1[C:15]([CH3:16])=[CH:14][C:11]([C:12]#[N:13])=[CH:10][C:9]=1[CH3:17].Cl>C(OCC)C.C1COCC1.O>[NH2:13][CH2:12][C:11]1[CH:10]=[C:9]([CH3:17])[C:8]([OH:7])=[C:15]([CH3:16])[CH:14]=1To a suspension of LiAlH4 (1.51 g, 39.8 mmol) in diethyl ether (40 mL) a solution of 4-hydroxy-3,5-dimethylbenzonitrile (4.89 g, 33.2 mmol) in diethyl ether (20 mL) and THF (10 mL) is added dropwise at rt. The mixture is stirred at rt for 22 h before it is cooled with an ice-bath and carefully treated with water (10 mL), acidified with 25% aq. HCl and diluted with water (30 mL). The mixture is extracted with diethyl ether. The etheral extract is discarded. The aqueous phase is basified to pH˜8 by adding solid NaHCO3, saturated with NaCl, and extracted with diethyl ether followed by EA. The combined organic extracts are dried over MgSO4 and evaporated to leave 4-aminomethyl-2,6-dimethyl-phenol (1.20 g) as a solid. LC-MS: tR=0.51 min, [M+1]+=152.19.
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