C([C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=1[I:18])[C:11]([O:13]C)=O)C1C=CC=CC=1.[BH4-].[Li+].[Cl-].[NH4+]>O1CCCC1>[CH2:11]([O:13][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=1[I:18])[CH2:11][OH:13])[C:10]1[CH:15]=[CH:16][CH:17]=[CH:8][CH:9]=1A solution of 139 g (374 mmol) of methyl 3-benzyl-4-iodobenzoate in 550 ml of tetrahydrofuran is added dropwise to a solution of 12.9 g (563 mmol) of lithium borohydride in 150 ml of tetrahydrofuran and the reaction medium is then refluxed for 3 hours. After cooling, 300 ml of saturated aqueous ammonium chloride solution are added and the reaction medium is extracted with ethyl acetate. The organic phase is washed with water, dried over sodium sulfate, filtered and evaporated. 125 g (97%) of 3-benzyloxy-4-iodobenzyl alcohol are obtained in the form of white crystals.
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