Hydrochloric Acid → Tyrosol

Temperature

0 °C

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%).

1. extractionthe reaction mixture was extracted with ethylacetate (200 ml×3)
2. washThe combined organic layer was washed with water (200 ml×2) and sat. NaCl (200 ml)
3. dry with materialdried over MgSO4
4. customThe dried organic layer was evaporated
5. customthe residue was purified by fresh column chromatography on silica gel (hexane/ethylacetate=3/1

ORD record

ord-496c8c5acb0b47a5887bee3978054d86

Source dataset

uspto-grants-2004_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06723798B1