1, 1,5-diphenyl-

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

Procedure: The 1,5-diphenyl-1,5-pentanedione prepared in step 1 (10 mmol, 2.52 g) is mixed with phosphorus pentasulfide (15 mmol, 3.34 g), acetic acid (60 mL) and lithium perchlorate (60 mmol, 6.40 g) in a 100 mL two-necked round-bottomed flask, and then refluxed for 3 hours. The solution then becomes orange and a white precipitate forms. The precipitate is removed by filtration on a sinter funnel and then washed with hot acetic acid. The solution is concentrated on a rotary evaporator and recrystallized by addition of ether (500 mL). The precipitate obtained is filtered off on a sinter funnel and then dried on a rotary evaporator. The product obtained is a yellow solid in a mass of 850 mg. The reaction yield is 24%. refluxed for 3 hours The precipitate is removed by filtration on a sinter funnel washed with hot acetic acid The solution is concentrated on a rotary evaporator recrystallized by addition of ether (500 mL) The precipitate obtained is filtered off on a sinter funnel dried on a rotary evaporator The product obtained The reaction yield is 24%

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

Procedure: A solution of glutaryl chloride (10 mmol, 1.3 mL) dissolved in anhydrous dichloromethane (20 mL) is introduced into a 100 mL two-necked round-bottomed flask under an inert atmosphere. Aluminum chloride (30 mmol, 4.00 g) is added to the mixture, which immediately turns orange-yellow. A solution of benzene (20 mmol, 1.8 mL) dissolved in anhydrous dichloromethane (10 mL) is added dropwise at room temperature. The solution becomes bright red. The mixture is then refluxed for 24 hours, and turns brown-black. The mixture is then cooled to room temperature and poured into a crystallizing basin containing 20 mL of 10% acidified water, with stirring. A black solid forms, and is filtered off on a Büchner funnel. The yellow organic phase is then extracted with ethyl acetate, dried over MgSO4, filtered, concentrated on a rotary evaporator and recrystallized from 20 mL of methanol. The product obtained is a white solid in a mass of 680 mg. The reaction yield is 27%. is introduced into a 100 mL two-necked round-bottomed flask under an inert atmosphere is added dropwise at room temperature The mixture is then refluxed for 24 hours poured into a crystallizing basin containing 20 mL of 10% A black solid forms, and is filtered off on a Büchner funnel The yellow organic phase is then extracted with ethyl acetate dried over MgSO4 filtered concentrated on a rotary evaporator recrystallized from 20 mL of methanol The product obtained The reaction yield is 27%

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

Procedure: The 1,5-diphenyl-1,5-pentanedione prepared in step 1 (10 mmol, 2.52 g) is mixed with phosphorus pentasulfide (15 mmol, 3.34 g), acetic acid (60 mL) and lithium perchlorate (60 mmol, 6.40 g) in a 100 mL two-necked round-bottomed flask, and then refluxed for 3 hours. The solution then becomes orange and a white precipitate forms. The precipitate is removed by filtration on a sinter funnel and then washed with hot acetic acid. The solution is concentrated on a rotary evaporator and recrystallized by addition of ether (500 mL). The precipitate obtained is filtered off on a sinter funnel and then dried on a rotary evaporator. The product obtained is a yellow solid in a mass of 850 mg. The reaction yield is 24%. refluxed for 3 hours The precipitate is removed by filtration on a sinter funnel washed with hot acetic acid The solution is concentrated on a rotary evaporator recrystallized by addition of ether (500 mL) The precipitate obtained is filtered off on a sinter funnel dried on a rotary evaporator The product obtained The reaction yield is 24%

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

Procedure: The 1,5-diphenyl-1,5-pentanedione prepared in step 1 (10 mmol, 2.52 g) is mixed with phosphorus pentasulfide (15 mmol, 3.34 g), acetic acid (60 mL) and lithium perchlorate (60 mmol, 6.40 g) in a 100 mL two-necked round-bottomed flask, and then refluxed for 3 hours. The solution then becomes orange and a white precipitate forms. The precipitate is removed by filtration on a sinter funnel and then washed with hot acetic acid. The solution is concentrated on a rotary evaporator and recrystallized by addition of ether (500 mL). The precipitate obtained is filtered off on a sinter funnel and then dried on a rotary evaporator. The product obtained is a yellow solid in a mass of 850 mg. The reaction yield is 24%. refluxed for 3 hours The precipitate is removed by filtration on a sinter funnel washed with hot acetic acid The solution is concentrated on a rotary evaporator recrystallized by addition of ether (500 mL) The precipitate obtained is filtered off on a sinter funnel dried on a rotary evaporator The product obtained The reaction yield is 24%

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

Procedure: A solution of glutaryl chloride (10 mmol, 1.3 mL) dissolved in anhydrous dichloromethane (20 mL) is introduced into a 100 mL two-necked round-bottomed flask under an inert atmosphere. Aluminum chloride (30 mmol, 4.00 g) is added to the mixture, which immediately turns orange-yellow. A solution of benzene (20 mmol, 1.8 mL) dissolved in anhydrous dichloromethane (10 mL) is added dropwise at room temperature. The solution becomes bright red. The mixture is then refluxed for 24 hours, and turns brown-black. The mixture is then cooled to room temperature and poured into a crystallizing basin containing 20 mL of 10% acidified water, with stirring. A black solid forms, and is filtered off on a Büchner funnel. The yellow organic phase is then extracted with ethyl acetate, dried over MgSO4, filtered, concentrated on a rotary evaporator and recrystallized from 20 mL of methanol. The product obtained is a white solid in a mass of 680 mg. The reaction yield is 27%. is introduced into a 100 mL two-necked round-bottomed flask under an inert atmosphere is added dropwise at room temperature The mixture is then refluxed for 24 hours poured into a crystallizing basin containing 20 mL of 10% A black solid forms, and is filtered off on a Büchner funnel The yellow organic phase is then extracted with ethyl acetate dried over MgSO4 filtered concentrated on a rotary evaporator recrystallized from 20 mL of methanol The product obtained The reaction yield is 27%

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

Procedure: While cooled by an ice-bath and stirred intensely, 0.0 mol 1,5-diphenyl-1,5-pentandione was added dropwise slowly to a mixture of 3 g LiAlH4 and 100 ml anhydrous tetrahydrofuran. The mixture was heated refluxing for 5 hours, then cooled. Excess LiAlH4 was decomposed with water. After mixing completely the reaction mixture with ethyl acetate, the mixture was filtered, and the filtrate was dried over anhydrous sodium sulfate. The solvent was removed. Column chromatography gave 1,5-diphenyl-1,5-pentanediol as a white solid, and the yield was 85%. mp: 64-67° C. IR spectrum had a strong —OH absorption peak at 3400 cm−1, and had no —CO— absorption peak at about 1700 cm−1. This demonstrated that the reduction reaction was carried out completely. While cooled by an ice-bath The mixture was heated refluxing for 5 hours cooled the mixture was filtered the filtrate was dried over anhydrous sodium sulfate The solvent was removed

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

Procedure: While cooled by an ice-bath and stirred intensely, 0.0 mol 1,5-diphenyl-1,5-pentandione was added dropwise slowly to a mixture of 3 g LiAlH4 and 100 ml anhydrous tetrahydrofuran. The mixture was heated refluxing for 5 hours, then cooled. Excess LiAlH4 was decomposed with water. After mixing completely the reaction mixture with ethyl acetate, the mixture was filtered, and the filtrate was dried over anhydrous sodium sulfate. The solvent was removed. Column chromatography gave 1,5-diphenyl-1,5-pentanediol as a white solid, and the yield was 85%. mp: 64-67° C. IR spectrum had a strong —OH absorption peak at 3400 cm−1, and had no —CO— absorption peak at about 1700 cm−1. This demonstrated that the reduction reaction was carried out completely. While cooled by an ice-bath The mixture was heated refluxing for 5 hours cooled the mixture was filtered the filtrate was dried over anhydrous sodium sulfate The solvent was removed

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

Procedure: Glutaryl chloride (28.2 g; 0.167 mole) was slowly added to a mixture of anhydrous aluminum trichloride (50 g; 0.375 mole) and 250 ml benzene. The mixture was stirred vigorously in an ice/water bath. After completion of the addition, the ice/water bath was removed and stirring was continued for two hours. The solution obtained was slowly poured into a mixture of 200 g crushed ice and 40 ml concentrated aqueous hydrochloric acid. The resulting product was recovered by extraction and crystallization to produce 1,5-diphenyl-1,5-pentanedione. After completion of the addition the ice/water bath was removed stirring The solution obtained was slowly poured into a mixture of 200 g The resulting product was recovered by extraction and crystallization

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

Procedure: The 1,5-diphenyl-1,5-pentanedione prepared in step 1 (10 mmol, 2.52 g) is mixed with phosphorus pentasulfide (15 mmol, 3.34 g), acetic acid (60 mL) and lithium perchlorate (60 mmol, 6.40 g) in a 100 mL two-necked round-bottomed flask, and then refluxed for 3 hours. The solution then becomes orange and a white precipitate forms. The precipitate is removed by filtration on a sinter funnel and then washed with hot acetic acid. The solution is concentrated on a rotary evaporator and recrystallized by addition of ether (500 mL). The precipitate obtained is filtered off on a sinter funnel and then dried on a rotary evaporator. The product obtained is a yellow solid in a mass of 850 mg. The reaction yield is 24%. refluxed for 3 hours The precipitate is removed by filtration on a sinter funnel washed with hot acetic acid The solution is concentrated on a rotary evaporator recrystallized by addition of ether (500 mL) The precipitate obtained is filtered off on a sinter funnel dried on a rotary evaporator The product obtained The reaction yield is 24%

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

Procedure: A solution of glutaryl chloride (10 mmol, 1.3 mL) dissolved in anhydrous dichloromethane (20 mL) is introduced into a 100 mL two-necked round-bottomed flask under an inert atmosphere. Aluminum chloride (30 mmol, 4.00 g) is added to the mixture, which immediately turns orange-yellow. A solution of benzene (20 mmol, 1.8 mL) dissolved in anhydrous dichloromethane (10 mL) is added dropwise at room temperature. The solution becomes bright red. The mixture is then refluxed for 24 hours, and turns brown-black. The mixture is then cooled to room temperature and poured into a crystallizing basin containing 20 mL of 10% acidified water, with stirring. A black solid forms, and is filtered off on a Büchner funnel. The yellow organic phase is then extracted with ethyl acetate, dried over MgSO4, filtered, concentrated on a rotary evaporator and recrystallized from 20 mL of methanol. The product obtained is a white solid in a mass of 680 mg. The reaction yield is 27%. is introduced into a 100 mL two-necked round-bottomed flask under an inert atmosphere is added dropwise at room temperature The mixture is then refluxed for 24 hours poured into a crystallizing basin containing 20 mL of 10% A black solid forms, and is filtered off on a Büchner funnel The yellow organic phase is then extracted with ethyl acetate dried over MgSO4 filtered concentrated on a rotary evaporator recrystallized from 20 mL of methanol The product obtained The reaction yield is 27%

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

Procedure: While cooled by an ice-bath and stirred intensely, 0.0 mol 1,5-diphenyl-1,5-pentandione was added dropwise slowly to a mixture of 3 g LiAlH4 and 100 ml anhydrous tetrahydrofuran. The mixture was heated refluxing for 5 hours, then cooled. Excess LiAlH4 was decomposed with water. After mixing completely the reaction mixture with ethyl acetate, the mixture was filtered, and the filtrate was dried over anhydrous sodium sulfate. The solvent was removed. Column chromatography gave 1,5-diphenyl-1,5-pentanediol as a white solid, and the yield was 85%. mp: 64-67° C. IR spectrum had a strong —OH absorption peak at 3400 cm−1, and had no —CO— absorption peak at about 1700 cm−1. This demonstrated that the reduction reaction was carried out completely. While cooled by an ice-bath The mixture was heated refluxing for 5 hours cooled the mixture was filtered the filtrate was dried over anhydrous sodium sulfate The solvent was removed