Diethyl Ether → 1-(2-Hydroxy-6-methylphenyl)ethanone

A solution of methyl magnesium bromide 3M in diethyl ether (18.5 mL, 55.5 mmol) and triethylamine (6.0 mL, 44.4 mmol) in anhydrous toluene (14 mL) was cooled to 0° C. 6-methylsalicylic acid ethyl ester (2.0 g, 11.1 mmol) in anhydrous toluene (14 mL) was added dropwise and the reaction mixture was stirred at room temperature for 16 hours. A saturated solution of ammonium chloride (10 mL) was added and the mixture was filtered over Celite®. The filtrate was diluted with ethyl acetate (20 mL) and water (10 mL) and layers were separated. The organic layer was washed with brine (10 mL), dried over sodium sulfate and evaporated to dryness. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate: 9/1) to provide the desired ketone (26a) (1.21 g, 8.0 mmol, 72%).

1. filtrationthe mixture was filtered over Celite®
2. additionThe filtrate was diluted with ethyl acetate (20 mL) and water (10 mL) and layers
3. customwere separated
4. washThe organic layer was washed with brine (10 mL)
5. dry with materialdried over sodium sulfate
6. customevaporated to dryness
7. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate: 9/1)

ORDレコード

ord-b494766faafc49a280d668843bc62aec

出典データセット

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09238026B2