[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[C:13]([CH3:19])[CH:12]=1)[CH:8]=[CH2:9].[Cl-].[NH4+].Cl>C1COCC1>[CH2:7]([O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][OH:16])=[C:13]([CH3:19])[CH:12]=1)[CH:8]=[CH2:9]
8.50 g (224 mmol) lithium aluminium hydride were given to 250 ml THF and stirred for 20 min. A solution of 19.4 g (110 mmol) 4-allyloxy-2-methyl-benzaldehyde in 100 ml THF was added dropwise and stirring continued for 3 h. The reaction mixture was cooled to 0° C., carefully hydrolysed with 40 ml concentrated ammonium chloride solution, stirred for 60 min. and adjusted to pH=5 with conc. hydrochloric acid. A formed salt precipitate was removed by filtration, washed with THF and the combined organic solutions evaporated. Chromatography of the residue on silica (n-heptane/ethyl acetate 1:3) gave 16.0 g (81%) (4-allyloxy-2-methyl-phenyl)-methanol as a slightly yellow oil.
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