Hydrogen Peroxide → HCID 59578505, compound

Under nitrogen atmosphere, a solution of 6-chloro-3-methyl-2-(prop-2-en-1-yl)phenol (7b) (8.70 g, 47.6 mmol) in anhydrous tetrahydrofuran (300 mL) was cooled to 0° C. Borane-tetrahydrofuran complex, 1.0M solution in tetrahydrofuran (100 mL, 0.10 mol) was dropwise added. The reaction mixture was stirred at room temperature for 2 hours then cooled again to 0° C. A 10N sodium hydroxide solution (32.7 mL) was added dropwise, followed by a 30% hydrogen peroxide solution. The resulting mixture was warm to room temperature and stirred for 90 minutes. The reaction mixture was quenched with a 10% hydrochloric acid solution (163 mL). Layers were separated and the aqueous layer was extract with ethyl acetate (2×70 mL). The combined organics layers were washed with brine (3×100 mL) then cooled with an ice bath. A saturated solution of sodium sulfite (150 mL) was carefully added and the mixture was stirred for few minutes. The organic layer was separated, dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100/0 to 75/25), to provide 6-chloro-2-(3-hydroxypropyl)-3-methylphenol (7c) (6.74 g, 33.6 mmol, 70%).

1. temperaturethen cooled again to 0° C
2. temperatureThe resulting mixture was warm to room temperature
3. stirringstirred for 90 minutes
4. customThe reaction mixture was quenched with a 10% hydrochloric acid solution (163 mL)
5. customLayers were separated
6. extractionthe aqueous layer was extract with ethyl acetate (2×70 mL)
7. washThe combined organics layers were washed with brine (3×100 mL)
8. temperaturethen cooled with an ice bath
9. additionA saturated solution of sodium sulfite (150 mL) was carefully added
10. stirringthe mixture was stirred for few minutes
11. customThe organic layer was separated
12. dry with materialdried over sodium sulfate
13. concentrationconcentrated in vacuo
14. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100/0 to 75/25)

ORD record

ord-af6fd4d3bfb04ce6a37fb205a2c51ea9

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09260395B2