Hydrochloric Acid → Tyrosol

Participants

Reaction Conditions

Reaction Steps

Methyl-4-hydroxyphenyl acetate (23.0 g, 139.0 mmol) was dissolved in THF (400 ml). After cooling to 0° C., lithium aluminum hydride (LAH; 7.9 g, 209.0 mmol) was added over 1 hr, stirred for 2 hrs at 0° C. and additionally for 8 hrs at room temperature. 1N aqueous HCl (300 ml) was added at 0° C. and the reaction mixture was extracted with ethylacetate (200 ml×3). The combined organic layer was washed with water (200 ml×2) and sat. NaCl (200 ml) and dried over MgSO4. The dried organic layer was evaporated and the residue was purified by fresh column chromatography on silica gel (hexane/ethylacetate=3/1, v/v) to obtain white solid of the desired product, 4-hydroxyphenethyl alcohol (16.3 g, 118.0 mmol, yield 85%).

Provenance & Evidence