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0 °C

8.50 g (224 mmol) lithium aluminium hydride were given to 250 ml Tetrahydrofuran (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.

1. stirringstirring
2. waitcontinued for 3 h
3. stirringstirred for 60 min.
4. customA formed salt precipitate was removed by filtration
5. washwashed with THF
6. customthe combined organic solutions evaporated