1-(2,4,6-trihydroxyphenyl)ethanone

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 250 ml of anhydrous tetrahydrofuran was dissolved 50.0 g of 2',4',6'-trihydroxyacetophenone, and 123.15 g of anhydrous potassium carbonate was added to the solution and the mixture was stirred at room temperature for 30 minutes. Then, 37.23 g of 1-chloro-3-methyl-2-butene was dropped into the solution over a period of 20 minutes and a reaction was carried out at room temperature for 24 hours. After the reaction, the reaction mixture was extracted with 2 l of ethyl acetate, and the ethyl acetate layer was washed with water (500 ml×4 times), shaken with a saturated aqueous solution of sodium chloride (300 ml×2 times), dried with anhydrous sodium sulfate and filtered. The solvent was removed from the filtrate by distillation and the obtained residue was recrystallized from a mixed solvent of benzene and petroleum ether to obtain 38.6 g (yield=55.0%) of 2',4',6'-trihydroxy-3'-(3-methyl-2-butenyl)acetophenone in the form of a yellow prism. was added to the solution a reaction was carried out at room temperature for 24 hours After the reaction the reaction mixture was extracted with 2 l of ethyl acetate the ethyl acetate layer was washed with water (500 ml×4 times) shaken with a saturated aqueous solution of sodium chloride (300 ml×2 times) dried with anhydrous sodium sulfate filtered The solvent was removed from the filtrate by distillation the obtained residue was recrystallized from a mixed solvent of benzene and petroleum ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 250 ml of anhydrous tetrahydrofuran was dissolved 50.0 g of 2',4',6'-trihydroxyacetophenone, and 123.15 g of anhydrous potassium carbonate was added to the solution and the mixture was stirred at room temperature for 30 minutes. Then, 37.23 g of 1-chloro-3-methyl-2-butene was dropped into the solution over a period of 20 minutes and a reaction was carried out at room temperature for 24 hours. After the reaction, the reaction mixture was extracted with 2 l of ethyl acetate, and the ethyl acetate layer was washed with water (500 ml×4 times), shaken with a saturated aqueous solution of sodium chloride (300 ml×2 times), dried with anhydrous sodium sulfate and filtered. The solvent was removed from the filtrate by distillation and the obtained residue was recrystallized from a mixed solvent of benzene and petroleum ether to obtain 38.6 g (yield=55.0%) of 2',4',6'-trihydroxy-3'-(3-methyl-2-butenyl)acetophenone in the form of a yellow prism. was added to the solution a reaction was carried out at room temperature for 24 hours After the reaction the reaction mixture was extracted with 2 l of ethyl acetate the ethyl acetate layer was washed with water (500 ml×4 times) shaken with a saturated aqueous solution of sodium chloride (300 ml×2 times) dried with anhydrous sodium sulfate filtered The solvent was removed from the filtrate by distillation the obtained residue was recrystallized from a mixed solvent of benzene and petroleum ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 200 ml of anhydrous tetrahydrofuran were dissolved 30 g of 2',4',6'-trihydroxyacetophenone and 115.0 g of N,N-diisopropylethylamine, and 50.2 g of chloromethyl methyl ether was gradually added to the solution under ice cooling over a period of 20 minutes and the reaction mixture was stirred under ice cooling for 1 hour and at room temperature for 4 hours to effect reaction. After the reaction, the reaction mixture was extracted with 3 l of ether, and the ether layer was washed with water (500 ml×3 times), shaken with a saturated aqueous solution of sodium chloride (300 ml×2 times), dried with anhydrous sodium sulfate, and filtered. The solvent was removed from the filtrate by distillation and the obtained residue was recrystallized from a mixed solvent of methanol and water to obtain 18.9 g (yield=41.4%) of 2'-hydroxy-4',6'-bis(methoxyacetophenone in the form of a colorless prism. was gradually added to the solution under ice cooling over a period of 20 minutes reaction After the reaction the reaction mixture was extracted with 3 l of ether the ether layer was washed with water (500 ml×3 times) shaken with a saturated aqueous solution of sodium chloride (300 ml×2 times) dried with anhydrous sodium sulfate filtered The solvent was removed from the filtrate by distillation the obtained residue was recrystallized from a mixed solvent of methanol and water

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 15 ml of anhydrous tetrahydrofuran was dissolved 3.0 g of 2',4',6'-trihydroxyacetophenone, and 7.4 g of anhydrous potassium carbonate was added to the solution and the mixture was stirred at room temperature for 30 minutes. Then, 2.5 g of 3-bromo-1-propene was added to the mixture and reaction was carried out at room temperature for 3 hours. After the reaction, the reaction mixture was extracted with 500 ml of diethyl ether, and the solvent was removed from the extract by distillation. The obtained residue was recrystallized from benzene to obtain 1.5 g (yield=41.5%) of 2',4',6'-trihydroxy-3'-(2-propenyl)acetophenone in the form of a colorless prism. was added to the solution was carried out at room temperature for 3 hours After the reaction the reaction mixture was extracted with 500 ml of diethyl ether the solvent was removed from the extract by distillation The obtained residue was recrystallized from benzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 15 ml of anhydrous tetrahydrofuran was dissolved 3.0 g of 2',4',6'-trihydroxyacetophenone, and 7.4 g of anhydrous potassium carbonate was added to the solution and the mixture was stirred at room temperature for 30 minutes. Then, 2.5 g of 3-bromo-1-propene was added to the mixture and reaction was carried out at room temperature for 3 hours. After the reaction, the reaction mixture was extracted with 500 ml of diethyl ether, and the solvent was removed from the extract by distillation. The obtained residue was recrystallized from benzene to obtain 1.5 g (yield=41.5%) of 2',4',6'-trihydroxy-3'-(2-propenyl)acetophenone in the form of a colorless prism. was added to the solution was carried out at room temperature for 3 hours After the reaction the reaction mixture was extracted with 500 ml of diethyl ether the solvent was removed from the extract by distillation The obtained residue was recrystallized from benzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 250 ml of anhydrous tetrahydrofuran was dissolved 50.0 g of 2',4',6'-trihydroxyacetophenone, and 123.1 g of anhydrous potassium carbonate was added to the solution and the mixture was stirred at room temperature for 30 minutes. Then, 37.2 g of 1-chloro3-methyl-2-butene was added dropwise to the mixture over a period of 20 minutes and reaction was carried out at room temperature for 24 hours. After the reaction, the reaction mixture was extracted with 2 l of ethyl acetate and the solvent was removed from the ethyl acetate layer by distillation, and the residue was recrystallized from a benzene/petroleum ether mixed solvent to obtain 38.6 g (yield=55.0%) of 2',4',6'-trihydroxy-3'-(3-methyl-2-butenyl)acetophenone in the form of a yellow prism. was added to the solution reaction was carried out at room temperature for 24 hours After the reaction the reaction mixture was extracted with 2 l of ethyl acetate the solvent was removed from the ethyl acetate layer by distillation the residue was recrystallized from a benzene/petroleum ether mixed solvent

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In tetrahydrofuran were dissolved and suspended 66.5 g of 2',4',6'-trihydroxyacetophenone and 173.0 g of potassium carbonate, and 56.0 ml of 1-chloro-3-methyl-2-butene was dropped into the solution. The mixture was stirred at room temperature for 2 hours and extracted with dimethyl ether, and the organic layer was washed with a 5% solution of potassium carbonate and then with water. The organic layer was shaken with a saturated solution of sodium chloride, dried with anhydrous sodium sulfate and concentrated under a reduced pressure. Recrystallization from benzene gave 31.8 g (yield=34.0%) of 2',4',6'-trihydroxy-3'-(3-methyl-2-butenyl)acetophenone. was dropped into the solution extracted with dimethyl ether the organic layer was washed with a 5% solution of potassium carbonate The organic layer was shaken with a saturated solution of sodium chloride dried with anhydrous sodium sulfate concentrated under a reduced pressure Recrystallization from benzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In tetrahydrofuran were dissolved and suspended 66.5 g of 2',4',6'-trihydroxyacetophenone and 173.0 g of potassium carbonate, and 56.0 ml of 1-chloro-3-methyl-2-butene was dropped into the solution. The mixture was stirred at room temperature for 2 hours and extracted with dimethyl ether, and the organic layer was washed with a 5% solution of potassium carbonate and then with water. The organic layer was shaken with a saturated solution of sodium chloride, dried with anhydrous sodium sulfate and concentrated under a reduced pressure. Recrystallization from benzene gave 31.8 g (yield=34.0%) of 2',4',6'-trihydroxy-3'-(3-methyl-2-butenyl)acetophenone. was dropped into the solution extracted with dimethyl ether the organic layer was washed with a 5% solution of potassium carbonate The organic layer was shaken with a saturated solution of sodium chloride dried with anhydrous sodium sulfate concentrated under a reduced pressure Recrystallization from benzene

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of dimethoxymethane (66 mL, 745 mmol) and zinc bromide (0.5 g) in DCM (580 mL) was added drop wise acetyl chloride (53 mL, 745 mmol) during half an hour maintaining the temperature under 20° C. After stirring 3 hours at room temperature, the solution was diluted with DCM (1200 mL), then cooled at 5° C. before the portion wise addition of 1-(2,4,6-trihydroxyphenyl)ethanone (phloroacetophenone) (50 g, 208 mmol) followed by the drop wise addition of DIPEA (208 mL, 1.19 mol). The resulting cloudy solution was stirred overnight, and then was washed with a NH4Cl saturated solution followed by washing with 10% citric acid solution. After drying over Na2SO4, the solvent was removed and the residue (78 g) nearly pure was used for the next step. The resulting cloudy solution was stirred overnight was washed with a NH4Cl saturated solution by washing with 10% citric acid solution After drying over Na2SO4 the solvent was removed

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of dimethoxymethane (66 mL, 745 mmol) and zinc bromide (0.5 g) in DCM (580 mL) was added drop wise acetyl chloride (53 mL, 745 mmol) during half an hour maintaining the temperature under 20° C. After stirring 3 hours at room temperature, the solution was diluted with DCM (1200 mL), then cooled at 5° C. before the portion wise addition of 1-(2,4,6-trihydroxyphenyl)ethanone (phloroacetophenone) (50 g, 208 mmol) followed by the drop wise addition of DIPEA (208 mL, 1.19 mol). The resulting cloudy solution was stirred overnight, and then was washed with a NH4Cl saturated solution followed by washing with 10% citric acid solution. After drying over Na2SO4, the solvent was removed and the residue (78 g) nearly pure was used for the next step. The resulting cloudy solution was stirred overnight was washed with a NH4Cl saturated solution by washing with 10% citric acid solution After drying over Na2SO4 the solvent was removed

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1.68g of phloroacetophenone and 12.7 g of benzyl chloride in 20 ml of DMF is added 5.53 g of anhydrous K2CO3. The mixture is stirred for 16 hours at 65° under argon. The mixture is diluted with 100 ml of 5% NaCl and extracted with ethyl acetate (2 × 50 ml). The extracts are washed with 5% NaCl and 2% NaOH, dried over MgSO4 and concentrated to a red oil which is purified on a dry 250 g silica gel columning CCl4 as eluent. This yields 2,4,6-tribenzyloxyacetophenone as a yellow oil. extracted with ethyl acetate (2 × 50 ml) The extracts are washed with 5% NaCl and 2% NaOH dried over MgSO4 concentrated to a red oil which is purified on a dry 250 g silica gel

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 250 ml of anhydrous tetrahydrofuran was dissolved 50.0 g of 2',4',6'-trihydroxyacetophenone, and 123.15 g of anhydrous potassium carbonate was added to the solution and the mixture was stirred at room temperature for 30 minutes. Then, 37.23 g of 1-chloro-3-methyl-2-butene was dropped into the solution over a period of 20 minutes and a reaction was carried out at room temperature for 24 hours. After the reaction, the reaction mixture was extracted with 2 l of ethyl acetate, and the ethyl acetate layer was washed with water (500 ml×4 times), shaken with a saturated aqueous solution of sodium chloride (300 ml×2 times), dried with anhydrous sodium sulfate and filtered. The solvent was removed from the filtrate by distillation and the obtained residue was recrystallized from a mixed solvent of benzene and petroleum ether to obtain 38.6 g (yield=55.0%) of 2',4',6'-trihydroxy-3'-(3-methyl-2-butenyl)acetophenone in the form of a yellow prism. was added to the solution a reaction was carried out at room temperature for 24 hours After the reaction the reaction mixture was extracted with 2 l of ethyl acetate the ethyl acetate layer was washed with water (500 ml×4 times) shaken with a saturated aqueous solution of sodium chloride (300 ml×2 times) dried with anhydrous sodium sulfate filtered The solvent was removed from the filtrate by distillation the obtained residue was recrystallized from a mixed solvent of benzene and petroleum ether