Water → 1-[2-(Methoxymethoxy)phenyl]ethan-1-one

In N,N-dimethylformamide (25 mL) was dissolved 3.39 g (24.9 mmol) of commercially available 1-(2-hydroxyphenyl)-ethanone, 1.52 g (38.0 mmol) of 60% sodium hydride was added to the solution in an ice bath, and the resulting mixture was stirred in an ice bath for 20 minutes. To the mixture was gradually added dropwise 3.00 mL (39.5 mmol) of chloro(methoxy)methane, and the resulting mixture was stirred at room temperature overnight. The reaction mixture was poured into water, and extracted with ethyl acetate. The organic layer was successively washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed, and the obtained residue was purified by silica gel column chromatography (Wako gel C-100, hexane-ethyl acetate, gradient) to obtain 4.33 g (24.1 mmol, Yield: 96.8%) of 1-[2-(methoxymethoxy)phenyl]ethanone.

1. additionwas added to the solution in an ice bath
2. stirringthe resulting mixture was stirred at room temperature overnight
3. extractionextracted with ethyl acetate
4. washThe organic layer was successively washed with water and brine
5. dry with materialdried over anhydrous magnesium sulfate
6. customThe solvent was removed
7. customthe obtained residue was purified by silica gel column chromatography (Wako gel C-100, hexane-ethyl acetate, gradient)

ORD record

ord-8d5f7d3c33654b4c894e4da997e76a1a

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07608563B2