[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:18]=[CH:17][C:11]([C:12](OCC)=[O:13])=[C:10]([O:19][CH2:20][CH3:21])[CH:9]=1.O.[OH-].[Na+]>O1CCCC1>[Cl:7][C:8]1[CH:18]=[CH:17][C:11]([CH2:12][OH:13])=[C:10]([O:19][CH2:20][CH3:21])[CH:9]=1To a stirred suspension of lithium aluminum hydride (4.12 g, 0.108 mol) in dry tetrahydrofuran under an atmosphere of nitrogen cooled to 5° C. is added a solution of ethyl 4-chloro-2-ethoxybenzoate (12.4 g, 54.24 mmol) in dry tetrahydrofuran (20 ml) dropwise over 15 min. The suspension is stirred at room temperature overnight then cooled to 0° C. and water (4.12 ml), aq. 15% sodium hydroxide (4.12 ml) and water (12.4 ml) added dropwise. The resulting suspension is filtered through celite and washed with ethyl acetate. Evaporate to give a colourless oil that crystallises on standing, triturate with iso-hexane and filter to give 4-chloro-2-ethoxybenzyl alcohol as a colourless solid.
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