2,6-Dichlorobenzoic acid → 2,6-Dichlorobenzoxymethylketone

The bromomethylketone derivative (4.36 g) and 2,6-dichlorobenzoic acid (2.28 g, 1.1 eq) were dissolved in dimethylformamide (18 mL), KF (1.58 g, 2.5 eq) was added thereto, and the mixture was stirred for 2 h at room temperature. The residue obtained by concentration under reduced pressure was extracted with ethyl acetate, washed with water, twice with saturated aqueous sodium hydrogen carbonate solution, and aqueous sodium chloride solution, dried (anhydrous Na2SO4), and concentrated under reduced pressure to give the 2,6-dichlorobenzoxymethylketone derivative. This compound was dissolved in methanol (20 mL), and reacted by adding NaBH4 (412 mg)-methanol solution (40 mL). The reaction mixture was slowly warmed to room temperature for 2 h. The reaction was stopped by acetic acid. The reaction mixture was distilled under reduced pressure to remove methanol, extracted with ethyl acetate (50 mL×2), washed with water and aqueous sodium chloride solution, dried (anhydrous Na2SO4), concentrated under reduced pressure, and separated by column chromatography (ethyl acetate-hexane, 1:5) to give 4.80 g (86%) of the title compound.

1. customThe residue obtained by concentration under reduced pressure
2. extractionwas extracted with ethyl acetate
3. washwashed with water, twice with saturated aqueous sodium hydrogen carbonate solution, and aqueous sodium chloride solution
4. dry with materialdried (anhydrous Na2SO4)
5. concentrationconcentrated under reduced pressure

ORDレコード

ord-1c66c55cd3054a8987ea98100c12c731

出典データセット

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08481537B2