m-Chloroperbenzoic acid → 2-Ethoxy-5-methylphenol

The solution of 14.5 g of 1-(2-ethoxy-5-methylphenyl)ethanone in 800 ml of dichloromethane is admixed with 36.8 g of 3-chloroperbenzoic acid and stirred at room temperature over 72 hours. The reaction mixture is concentrated by evaporation, and the residue is admixed with 400 ml of saturated aqueous sodium thiosulphate solution and extracted with tert-butyl methyl ether (2×800 ml). The organic phases are washed successively with saturated aqueous sodium carbonate solution (1×500 ml) and brine (500 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The residue is taken up in 75 ml of methanol, admixed with 25 ml of ammonia solution (25%) and stirred over 30 minutes. The reaction mixture is concentrated by evaporation, admixed with 0.5 M HCl (200 ml) and extracted with tert-butyl methyl ether (600 ml). The organic phase is washed with brine (500 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a brown solid from the residue by means of flash chromatography (SiO2 60F). Rt=3.89.

1. concentrationThe reaction mixture is concentrated by evaporation
2. extractionextracted with tert-butyl methyl ether (2×800 ml)
3. washThe organic phases are washed successively with saturated aqueous sodium carbonate solution (1×500 ml) and brine (500 ml)
4. dry with materialdried over sodium sulphate
5. filtrationfiltered
6. concentrationconcentrated by evaporation
7. stirringstirred over 30 minutes
8. concentrationThe reaction mixture is concentrated by evaporation
9. extractionextracted with tert-butyl methyl ether (600 ml)
10. washThe organic phase is washed with brine (500 ml)
11. dry with materialdried over sodium sulphate
12. filtrationfiltered
13. concentrationconcentrated by evaporation

ORD record

ord-20dc44dd9c314277b93575c96befdf82

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07790715B2