4-chlorobutyl acetate

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:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 4-Chlorobutyl acetate (276.6 g; 1.8 mol) is added to a solution of ethyl 4-hydroxybenzoate (249 g; 1.5 mol), potassium iodide (3 g) and potassium carbonate (248 g; 1.8 mol) in dimethylformamide (2 l), and the mixture is stirred at 90° C. for 11 hours. The reaction mixture is transferred into 5 l of ice water, and the resultant precipitate is filtered off with suction and washed with 4 to 5 l of ice water. The crude product is dissolved in 3 l of ethanol, potassium hydroxide (400 g) is added, and the mixture is refluxed for 3 hours. The reaction mixture is transferred into 6 l of ice water, and acidified by means of concentrated hydrochloric acid, and the precipitate is filtered off, washed with water until neutral and then dried. the resultant precipitate is filtered off with suction washed with 4 to 5 l of ice water The crude product is dissolved in 3 l of ethanol potassium hydroxide (400 g) is added the mixture is refluxed for 3 hours the precipitate is filtered off washed with water until neutral and then dried

反応条件: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 276.6 g of 4-chlorobutyl acetate (1.8 mol) were added to a solution of 249 g of ethyl 4-hydroxybenzoate (1.5 mol), 3 g of potassium iodide (0.018 mol) and 248 g of potassium carbonate (1.8 mol) in 21 of DMF, and the mixture was stirred at 90° C. for 11 hours. The reaction mixture was poured into 5 l of ice-water, and the precipitate was filtered off with suction and washed with 41 of ice-water. The crude product was dissolved in 3 l of ethanol, potassium hydroxide (400 g) was added, and the mixture was refluxed for 3 hours. The reaction mixture was poured into 6 l of ice-water and acidified using concentrated hydrochloric acid, and the precipitate was filtered off. The precipitate was washed with water until neutral and subsequently dried, giving 282.1 g of 4-(4′-hydroxybutoxy)benzoic acid (yield 89%). the precipitate was filtered off with suction washed with 41 of ice-water The crude product was dissolved in 3 l of ethanol potassium hydroxide (400 g) was added the mixture was refluxed for 3 hours The reaction mixture was poured into 6 l of ice-water the precipitate was filtered off The precipitate was washed with water until neutral and subsequently dried

反応条件: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 276.6 g of 4-chlorobutyl acetate (1.8 mol) were added to a solution of 249 g of ethyl 4-hydroxybenzoate (1.5 mol), 3 g of potassium iodide (0.018 mol) and 248 g of potassium carbonate (1.8 mol) in 21 of DMF, and the mixture was stirred at 90° C. for 11 hours. The reaction mixture was poured into 5 l of ice-water, and the precipitate was filtered off with suction and washed with 41 of ice-water. The crude product was dissolved in 3 l of ethanol, potassium hydroxide (400 g) was added, and the mixture was refluxed for 3 hours. The reaction mixture was poured into 6 l of ice-water and acidified using concentrated hydrochloric acid, and the precipitate was filtered off. The precipitate was washed with water until neutral and subsequently dried, giving 282.1 g of 4-(4′-hydroxybutoxy)benzoic acid (yield 89%). the precipitate was filtered off with suction washed with 41 of ice-water The crude product was dissolved in 3 l of ethanol potassium hydroxide (400 g) was added the mixture was refluxed for 3 hours The reaction mixture was poured into 6 l of ice-water the precipitate was filtered off The precipitate was washed with water until neutral and subsequently dried

反応条件: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a 1 L three neck distillation flask, p-hydroxybenzaldehyde (24.4 g, 20 mmol), 4-chlorobutylacetate (36.1 g, 240 mmol), potassium carbonate (33.2 g, 240 mmol) and dimethylformamido (150 ml) were placed and stirred for 3 hours at 120° C. After the reaction mixture was cooled, water was added and the resulting mixture was extracted with ethyl acetate. The solvent was removed to obtain an oily product. The product was dissolved in methanol (100 ml), and potassium hydroxide (22.4 g, 0.4 mmol) dissolved in water (50 ml) was dropwise added to the solution. The mixture was refluxed for 2 hours, and then cooled. Water was added and the resulting mixture was extracted with ethyl acetate. The solvent was removed to obtain an oily product. The product was purified through column chromatography to prepare the titled compound (35.3 g, yield: 91%). After the reaction mixture was cooled the resulting mixture was extracted with ethyl acetate The solvent was removed to obtain an oily product was dropwise added to the solution The mixture was refluxed for 2 hours cooled the resulting mixture was extracted with ethyl acetate The solvent was removed to obtain an oily product The product was purified through column chromatography

反応条件: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a 1 L three neck distillation flask, p-hydroxybenzaldehyde (24.4 g, 20 mmol), 4-chlorobutylacetate (36.1 g, 240 mmol), potassium carbonate (33.2 g, 240 mmol) and dimethylformamido (150 ml) were placed and stirred for 3 hours at 120° C. After the reaction mixture was cooled, water was added and the resulting mixture was extracted with ethyl acetate. The solvent was removed to obtain an oily product. The product was dissolved in methanol (100 ml), and potassium hydroxide (22.4 g, 0.4 mmol) dissolved in water (50 ml) was dropwise added to the solution. The mixture was refluxed for 2 hours, and then cooled. Water was added and the resulting mixture was extracted with ethyl acetate. The solvent was removed to obtain an oily product. The product was purified through column chromatography to prepare the titled compound (35.3 g, yield: 91%). After the reaction mixture was cooled the resulting mixture was extracted with ethyl acetate The solvent was removed to obtain an oily product was dropwise added to the solution The mixture was refluxed for 2 hours cooled the resulting mixture was extracted with ethyl acetate The solvent was removed to obtain an oily product The product was purified through column chromatography

反応条件: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a 1 L three neck distillation flask, p-hydroxybenzaldehyde (40.0 g, 328 mmol), 4-chlorobutylacetate (54.3 g, 360 mmol), potassium carbonate (45.3 g, 32.8 mmol) and dimethylformamido (150 ml) were placed and stirred for 3 hours at 120° C. After the reaction mixture was cooled, water was added and the resulting mixture was extracted with ethyl acetate. The solvent was removed to obtain an oily product. To the product, malonic acid (40.8 g, 392 mmol), pyrrolidine (10 ml) and pyridine (200 ml) were added and stirred for 2 hours at 120° C. The mixture was cooled to 60° C., and methanol (200 ml) and 40 wt. % potassium hydroxide aqueous solution (200 ml) were added and stirred for 2 hours at 60° C. The mixture was cooled, and then poured into a dilute hydrochloric acid (prepared by diluting 330 ml of concentrated hydrochloric acid with 4 L water) The deposited crystalline product was collected by filtration, and recrystallized from acetonitrile to obtain the titled compounds (65.6 g, yield: 85%). After the reaction mixture was cooled the resulting mixture was extracted with ethyl acetate The solvent was removed to obtain an oily product stirred for 2 hours at 120° C The mixture was cooled to 60° C. stirred for 2 hours at 60° C The mixture was cooled was collected by filtration recrystallized from acetonitrile

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

実験手順: Add anhydrous sodium sulfite (16.8 g, 130 mmol) to a solution of 4-chlorobutyl acetate (20.0 g, 133 mmol) in water (50 mL) and reflux the mixture for 20 h. Cool to room temperature and add concentrated HCl (19.0 mL) and reflux for 1 h. Cool the mixture to room temperature, neutralize to about pH=7. Concentrate to about one half the volume, filter away the sodium chloride. Concentrate and dry to give the title compound. reflux the mixture for 20 h reflux for 1 h Cool the mixture to room temperature Concentrate to about one half the volume filter away the sodium chloride Concentrate dry

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

実験手順: To a stirred slurry of 1.6 g sodium hydride (as 50% dispersion in oil) in 50 ml dry dimethyl formamide was added, dropwise, a solution of 5.0 g p-tert-butylphenol (33.3 mmoles) in 50 ml dry dimethyl formamide and the solution stirred under nitrogen until the phenoxide had totally formed. To the phenoxide was added a solution of 5.0 g 4-chlorobutyl acetate (33.3 mmoles) in 50 ml dry dimethyl formamide and the solution was stirred for fourteen hours. The reaction mixture was partitioned between water/toluene. The organic layer was removed, washed with water, then 1 N sodium bicarbonate. The organic layer was removed, dried and evaporated to an orange oil, 5.6 g. The oil was chromatographed on 500 g, 90 to 200 mesh silica gel (CH2Cl2 eluent) yielding pure 4-(p-tert-butylphenoxy)-butyl acetate. had totally formed The reaction mixture was partitioned between water/toluene The organic layer was removed washed with water The organic layer was removed dried evaporated to an orange oil, 5.6 g The oil was chromatographed on 500 g, 90 to 200 mesh silica gel (CH2Cl2 eluent)

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

実験手順: To a stirred slurry of 1.6 g sodium hydride (as 50% dispersion in oil) in 50 ml dry dimethyl formamide was added, dropwise, a solution of 5.0 g p-tert-butylphenol (33.3 mmoles) in 50 ml dry dimethyl formamide and the solution stirred under nitrogen until the phenoxide had totally formed. To the phenoxide was added a solution of 5.0 g 4-chlorobutyl acetate (33.3 mmoles) in 50 ml dry dimethyl formamide and the solution was stirred for fourteen hours. The reaction mixture was partitioned between water/toluene. The organic layer was removed, washed with water, then 1 N sodium bicarbonate. The organic layer was removed, dried and evaporated to an orange oil, 5.6 g. The oil was chromatographed on 500 g, 90 to 200 mesh silica gel (CH2Cl2 eluent) yielding pure 4-(p-tert-butylphenoxy)-butyl acetate. had totally formed The reaction mixture was partitioned between water/toluene The organic layer was removed washed with water The organic layer was removed dried evaporated to an orange oil, 5.6 g The oil was chromatographed on 500 g, 90 to 200 mesh silica gel (CH2Cl2 eluent)

反応条件: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 4-Chlorobutyl acetate (276.6 g; 1.8 mol) is added to a solution of ethyl 4-hydroxybenzoate (249 g; 1.5 mol), potassium iodide (3 g) and potassium carbonate (248 g; 1.8 mol) in dimethylformamide (2 l), and the mixture is stirred at 90° C. for 11 hours. The reaction mixture is transferred into 5 l of ice water, and the resultant precipitate is filtered off with suction and washed with 4 to 5 l of ice water. The crude product is dissolved in 3 l of ethanol, potassium hydroxide (400 g) is added, and the mixture is refluxed for 3 hours. The reaction mixture is transferred into 6 l of ice water, and acidified by means of concentrated hydrochloric acid, and the precipitate is filtered off, washed with water until neutral and then dried. the resultant precipitate is filtered off with suction washed with 4 to 5 l of ice water The crude product is dissolved in 3 l of ethanol potassium hydroxide (400 g) is added the mixture is refluxed for 3 hours the precipitate is filtered off washed with water until neutral and then dried