Hydrochloric Acid → 2-(3-Hydroxypropyl)-6-methylphenol

To a borane-tetrahydrofuran complex solution (100 mL, 1M solution) was added dropwise 2-allyl-6-methylphenol (21 g) under ice-cooling. After stirring at room temperature for 3 hours, a 2N aqueous sodium hydroxide solution (55 mL) and a 30% aqueous hydrogen peroxide solution (12 mL) were added to the reaction mixture under ice-cooling. After stirring overnight at room temperature, the reaction mixture was acidified with a 2N hydrochloric acid and extracted with diethyl ether. The organic layer was washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was purified by silica gel column chromatography and dried to give the title compound (15 g).

1. temperaturecooling
2. temperaturecooling
3. stirringAfter stirring overnight at room temperature
4. extractionextracted with diethyl ether
5. washThe organic layer was washed with brine
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. customevaporated
9. customThe residue was purified by silica gel column chromatography
10. customdried

ORD record

ord-1f60246f1d7945c9b02b09dcabb2bf5c

Source dataset

uspto-grants-1999_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05861437