1-(3-chloro-4-hydroxyphenyl)ethanone

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred solution of 2-chlorophenol (10.0 g, 77.8 mmol) in carbon disulfide (20 ml) was added aluminum chloride (21.8 g, 163.4 mmol) at 0° C. under nitrogen. Acetyl chloride (6.72 g, 85.6 mmol) was added, and the mixture was heated at reflux temperature for 6 hours. The mixture was cooled down to room temperature, and poured into ice-water. The whole was extracted with diethylether. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was recrystallized with diethylether-hexane to give the title compound (6.39 g, 48% yield). the mixture was heated at reflux temperature for 6 hours The whole was extracted with diethylether The organic layer was washed with brine dried over MgSO4 concentrated in vacuo The residue was recrystallized with diethylether-hexane

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of compound 133 (0.30 g, 0.78 mmol), potassium carbonate (0.54 g, 3.92 mmol) in dimethylformamide (10 mL) was added 3-chloro-4-hydroxyacetophenone (0.133 g, 0.78 mmol). It was heated to 80° C. for 12 hours with stirring under nitrogen atmosphere. The mixture was then cooled, diluted with water (20 mL) and extracted with EtOAc (2×20 mL). The combined organic layers were washed with water (2×10 mL), dried over anhydrous sodium sulphate and concentrated under vacuum. The residue thus obtained was purified by column chromatography to afford the title compound as white solid (0.08 g, 67%). mp 186-196° C.; HPLC: Inertsil ODS 3V (250×4.6 mm) 5 microns [mobile phase: 0.01 M KH2PO4: CH3CN (20:80)]; 212 nm, R, 12.33 min, 99.15% purity; MS (CI): m/z 516 (M+, 100). The mixture was then cooled extracted with EtOAc (2×20 mL) The combined organic layers were washed with water (2×10 mL) dried over anhydrous sodium sulphate concentrated under vacuum The residue thus obtained was purified by column chromatography

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred solution of 1-(3-chloro-4-hydroxylphenyl)ethanone (1.7 g, 10 mmol) in DMF was added K2CO3 (1.52 g, 11 mmol), 2 N NaOH solution (5 ml), and Mel (0.68 ml). The reaction mixture was stirred at room temperature for 2 hours. Another 1.24 ml of Mel was added, and the reaction mixture was stirred for an additional 30 minutes. Water (50 ml) was added, and the product was extracted with 200 ml of EtOAc and 100 ml of benzene. The organic layer was washed with brine (50 ml), and dried with MgSO4, and the solvent was removed in vacuo to give the title compound in quantitative yield. Another 1.24 ml of Mel was added the reaction mixture was stirred for an additional 30 minutes the product was extracted with 200 ml of EtOAc and 100 ml of benzene The organic layer was washed with brine (50 ml) dried with MgSO4 the solvent was removed in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred solution of 2-chlorophenol (10.0 g, 77.8 mmol) in carbon disulfide (20 ml) was added aluminum chloride (21.8 g, 163.4 mmol) at 0° C. under nitrogen. Acetyl chloride (6.72 g, 85.6 mmol) was added, and the mixture was heated at reflux temperature for 6 hours. The mixture was cooled down to room temperature, and poured into ice-water. The whole was extracted with diethylether. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was recrystallized with diethylether-hexane to give the title compound (6.39g, 48% yield). the mixture was heated at reflux temperature for 6 hours The whole was extracted with diethylether The organic layer was washed with brine dried over MgSO4 concentrated in vacuo The residue was recrystallized with diethylether-hexane

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A 500-milliliter flask was charged with 300 milliliters of concentrated sulfuric acid, chilled to 5° to 10° C. and at this temperature 17.1 grams of 3'-chloro-4'-hydroxyacetophenone was slowly added. To the stirred clear solution 20 grams of potassium nitrate was slowly added during a period of about 30-40 minutes while the temperature was maintained between 5° and 10° C. After stirring for an additional 45-60 minutes, the solution was stirred into 1,000 grams of ice. The resulting pale yellow solid was filtered and washed with water. was slowly added was maintained between 5° and 10° C The resulting pale yellow solid was filtered washed with water

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 50 gm of p-hydroxyacetophenone were dissolved in 500 ml of hot methylene dichloride and filtered through a small pad of silica gel. The solution was allowed to cool and the methylene dichloride was stripped off to obtain 41.75 gm (0.31 mol) of crystals. These crystals were dissolved in about 1.5 liters of methylene dichloride. The reaction flask was placed in an ice bath and chlorine gas was bubbled through the solution. After about a total of 5 minutes of Cl2(g) bubbling, the methylene chloride was stripped off to yield more than 30 gm of white crystals (>90% pure) of 3-chloro-4-hydroxy acetophenone. filtered through a small pad of silica gel to cool

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred solution of 2-chlorophenol (10.0 g, 77.8 mmol) in carbon disulfide (20 ml) was added aluminum chloride (21.8 g, 163.4 mmol) at 0° C. under nitrogen. Acetyl chloride (6.72 g, 85.6 mmol) was added, and the mixture was heated at reflux temperature for 6 hours. The mixture was cooled down to room temperature, and poured into ice-water. The whole was extracted with diethylether. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was recrystallized with diethylether-hexane to give the title compound (6.39 g, 48% yield). the mixture was heated at reflux temperature for 6 hours The whole was extracted with diethylether The organic layer was washed with brine dried over MgSO4 concentrated in vacuo The residue was recrystallized with diethylether-hexane