Chloromethyl Methyl Ether → 1-Methoxy-3-(methoxymethoxy)benzene

In N,N-dimethylformamide (50 mL) was dissolved 3.68 g (29.7 mmol) of commercially available 3-methoxyphenol, 1.81 g (45.4 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 in an ice bath 4.05 mL (53.3 mmol) of chloro(methoxy)methane, and the resulting mixture was stirred at room temperature overnight. To the reaction mixture was added a saturated aqueous ammonium chloride solution, and the mixture was 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 4.81 g (28.6 mmol, Yield: 96.3%) of 1-methoxy-3-(methoxymethoxy)benzene.

1. additionwas added to the solution in an ice bath
2. stirringthe resulting mixture was stirred at room temperature overnight
3. extractionthe mixture was extracted 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-25e32ea9ac55436580f5f6014495c30b

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07964531B2