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CAS No. : | 108807-05-2 |
Formula : | C17H17ClO2 |
M.W : | 288.77 |
SMILES Code : | O=C(Cl)C1=CC=C(OCCCCC2=CC=CC=C2)C=C1 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride; In toluene; | Production Example 2 Production of 3[4-(4-phenyl-1-butoxy)benzoyl]amino-2-hydroxyacetophenone To the solution of <strong>[30131-16-9]4-(4-phenyl-1-butoxy)benzoic acid</strong> in toluene obtained in Production Example 1, 12.9 g of thionyl chloride was added dropwise at room temperature, and the mixture was stirred at 40 C. for 30 minutes. After completion of the reaction, excess thionyl chloride and toluene were removed under reduced pressure, which afforded 4-(4-phenyl-1-butoxy)benzoyl chloride. | |
With thionyl chloride; In ISOPROPYLAMIDE; at 0℃; | <strong>[30131-16-9]4-(4-phenylbutoxy)benzoic acid</strong> (29.1 g; 1.1 equivalent ratio; prepared according to the method disclosed in US Pat. No. 4,780,469) was dissolved in 80 ml dimethylacetamide (DMAC, Aldrich) at 00C and then thionyl chloride (14.2 g, 1.2 equivalent ratio, Aldrich) was gradually added to the solution. After the mixture solution was stirred for 10 min at 00C, the mixture of 8-amino-4-oxo-tetrazol-5-yl-4H- 1-benzopyran hydrochloride salt (26.7 g; 1 equivalent ratio; prepared according to the method disclosed in US Pat. No. 4,780,469) and triethylamine (TEA, 10.1 g, 1 equivalent ratio, Aldrich) dissolved in 80 ml dimethylacetamide (DMAC, Aldrich) was slowly added to the mixture solution, and thermally stirred for 5 hrs at 25C. The reaction mixture was mixed with 300 ml H2O and stirred for 1 hr at 250C. The solid material obtained by filtering the solid material produced was washed with 100 ml H2O. 200 ml 50% acetone aqueous solution was added to the solid material and then refluxed for 1 hr. After the reaction mixture was cooled to room temperature, filtered and air-dried, the mixture was kept to stand on air for 5 hrs, obtaining 47.0 g pranlukart hemihydrates (yield rate: 98%): melting point 231-233C (decomposition); 1H-NMR (DMSO-d6, 300 MHz) delta 1.9 (m, 4H), 2,7 (m, 2H), 4.0 (t, 2H), 7.0 (s, 2H), 7.1 (s, IH), 7.2-7.3 (m, 5H), 7.6 (t, IH), 7.9 (t, IH), 8.0 (m, 2H), 8.3 (t, IH), 10.0 (bs, IH). | |
With oxalyl dichloride;N,N-dimethyl-formamide; at 20℃; for 2h; | To a suspension of <strong>[30131-16-9]4-(4-phenylbutoxy)benzoic acid</strong> (5.40 g) in methylene chloride (20 mL) were added oxalyl chloride (2.09 mL) and N,N-dimethylformamide (1 drop), and the resulting mixture was stirred for 2 hours at room temperature and then concentrated. To a suspension of the compound prepared in Example 3 (5.61 g) in methylene chloride (60 mL) were added pyridine (4.85 mL) and the previously prepared acid chloride in methylene chloride (20 mL), with ice cooling and the resulting mixture was stirred for 3 hours at room temperature. The reaction mixture was concentrated and the residue was diluted with ethyl acetate. The diluted solution was washed sequentially with water, 1N hydrochloric acid, water, saturated aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate and concentrated. The residue was recrystallized from a mixed solvent of ethyl acetate (100 mL) and n-hexane (100 mL) to give the title compound (8.58 g) having the following physical data. TLC: Rf 0.54 (n-hexane : ethyl acetate = 2 : 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium carbonate; In toluene; | (3) In a reactor, toluene (160 g) and 3-amino-2-hydroxyacetophenone (hereinafter referred to as "AHA") sulfate (the molecular weight, 249.3. 42.3 g) were charged and heated to 40 C. At the same temperature, to this solution, the solution of 4-(4-phenyl-1-butoxy)benzoyl chloride in toluene (79.3 g) obtained in the above step (2) and an aqueous solution of sodium carbonate (1.6 equivalents to <strong>[30131-16-9]4-(4-phenyl-1-butoxy)benzoic acid</strong>) were dropwise added simultaneously over a period of one hour, followed by heating at the same temperature for 2 hours. After the completion of the reaction, the reaction mixture was neutralized with hydrochloric acid. An organic layer was washed with water and phase separated. Then, the organic layer was cooled to 0 C. and maintained at that temperature to crystallize the product to obtain 3-[4-(4-phenyl-1-butoxy)benzoyl]amino-2-hydroxyacetophenone (66.8 g). Yield of the pure product, 97.3% (based on AHA sulfate). | |
With sodium carbonate; In toluene; | (3) In a reactor, toluene (80 g) and AHA hydrochloride (the molecular weight, 187.6. 15.9 g) were charged and heated to 40 C. At the same temperature, to this solution, the solution of 4-(4-phenyl-1-butoxy)benzoyl chloride in toluene (41.1 g) obtained in the above step (2) and an aqueous solution of sodium carbonate (1.2 equivalents to <strong>[30131-16-9]4-(4-phenyl-1-butoxy)benzoic acid</strong>) were dropwise added simultaneously over a period of one hour, followed by heating at the same temperature for 2 hours. After the completion of the reaction, the reaction mixture was neutralized with hydrochloric acid. An organic layer was washed with water and phase separated. Then, the organic layer was cooled to 0 C. and maintained at that temperature to crystallize the product to obtain 3-[4-(4-phenyl-1-butoxy)benzoyl]amino-2-hydroxyacetophenone (33.4 g). Yield of the pure product, 96.9% (based on AHA hydrochloride). | |
With sodium carbonate; In toluene; | (3) In a reactor, toluene (80 g) and AHA sulfate (21.3 g) were charged and heated to 40 C. At the same temperature, to this solution, the solution of 4-(4-phenyl-1-butoxy)benzoyl chloride in toluene (40.7 g) obtained in the above step (2) and an aqueous solution of sodium carbonate (1.6 equivalents to <strong>[30131-16-9]4-(4-phenyl-1-butoxy)benzoic acid</strong>) were dropwise added simultaneously over a period of one hour, followed by heating at the same temperature for 2 hours. After the completion of the reaction, the reaction mixture was neutralized with hydrochloric acid. An organic layer was washed with water and phase separated. Then, the organic layer was cooled to 0 C. and maintained at that temperature to crystallize the product to obtain 3-[4-(4-phenyl-1-butoxy)benzoyl]amino-2-hydroxyacetophenone (33.6 g). Yield of the pure product, 95.2% (based on <strong>[30131-16-9]4-(4-phenyl-1-butoxy)benzoic acid</strong>). |
With sodium carbonate; In toluene; | (3) In a reactor, toluene (80 g) and AHA hydrochloride (16.0 g) were charged and heated to 40 C. At the same temperature, to this solution, the solution of 4-(4-phenyl-1-butoxy)benzoyl chloride in toluene (41.4 g) obtained in the above step (2) and an aqueous solution of sodium carbonate (1.3 equivalents to <strong>[30131-16-9]4-(4-phenyl-1-butoxy)benzoic acid</strong>) were dropwise added simultaneously over a period of one hour, followed by heating at the same temperature for 2 hours. After the completion of the reaction, the reaction mixture was neutralized with hydrochloric acid. An organic layer was washed with water and phase separated. Then, the organic layer was cooled to 0 C. and maintained at that temperature to crystallize the product to obtain 3-[4-(4-phenyl-1-butoxy)benzoyl]amino-2-hydroxyacetophenone (32.1 g). Yield of the pure product, 93.3% (based on AHA hydrochloride). | |
With sodium carbonate; In toluene; | (3) In a reactor, toluene (162.0 g) and AHA sulfate (43.3 g) were charged and heated to 45 C. At the same temperature, to this solution, the solution of 4-(4-phenyl-1-butoxy)benzoyl chloride in toluene (146.5 g) obtained in the above step (2) and an aqueous solution of sodium carbonate (1.6 equivalents to <strong>[30131-16-9]4-(4-phenyl-1-butoxy)benzoic acid</strong>) were dropwise added simultaneously over a period of one hour, followed by heating at the same temperature for 2 hours. After the completion of the reaction, the reaction mixture was neutralized with hydrochloric acid. An organic layer was washed with water and separated. Then, the organic layer was cooled to 0 C. and maintained at that temperature to crystallize the product to obtain 3-[4-(4-phenyl-1-butoxy)benzoyl]amino-2-hydroxyacetophenone (68.8 g). Yield of the pure product, 96.7% (from the step (2), based on <strong>[30131-16-9]4-(4-phenyl-1-butoxy)benzoic acid</strong>). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; N,N-dimethyl-formamide; | REFERENCE EXAMPLE 12 STR54 One drop of N,N-dimethylformamide was added to a solution of 1 g of <strong>[30131-16-9]p-(4-phenylbutoxy)benzoic acid</strong> in 5 ml of methylene chloride and 2 ml of oxalyl chloride was added to the mixture at -30 C. or lower. The mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure to obtain crude p-(4-phenylbutoxy)benzoyl chloride. | |
In dichloromethane; N,N-dimethyl-formamide; | REFERENCE EXAMPLE 27 STR97 One drop of N,N-dimethylformamide was added to a solution of 1.41 g of <strong>[30131-16-9]p-(4-phenylbutoxy)benzoic acid</strong> in 35 ml of methylene chloride and 1.5 ml of oxalyl chloride was further added to the mixture under ice cooling. The mixture was stirred for 30 minutes and at room temperature for an additional 1 hour. The reaction mixture was concentrated under reduced pressure to obtain crude p-(4-phenylbutoxy)benzoyl chloride. |
Tags: 108807-05-2 synthesis path| 108807-05-2 SDS| 108807-05-2 COA| 108807-05-2 purity| 108807-05-2 application| 108807-05-2 NMR| 108807-05-2 COA| 108807-05-2 structure
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