[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][O:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][CH:8]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[CH2:5][O:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11][OH:12])=[CH:9][CH:8]=1
A solution of 3.79 g of 4-(3-fluoro-benzyloxy)-benzaldehyde in 10 ml of tetrahydrofurane was added dropwise at room temperature to a suspension of 1.25 g of lithium-aluminiumhydride in 40 ml of tetrahydrofurane. After 2 h at room temperature, successively 1.25 ml of water were added dropwise under cooling, then 3.75 ml of a sodium hydroxide solution (1 N), finally, 1.25 ml of water. The mixture was filtered over a layer of Dicalit and the tetrahydrofurane distilled off the solution under reduced pressure. The residual phase was extracted with ethyl acetate, the combined organic layers were dried over magnesium sulphate und evaporated under reduced pressure. The residue was crystallised from a mixture of ether and n-hexane to yield 2.26 g (59% of theory) of [4-(3-fluoro-benzyloxy)-phenyl]-methanol as a white solid; MS: m/e=232 (M)+.
Loading…
