ethyl 5-phenylpentanoate

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

Procedure: 250 g (1.4 moles) of 5-phenylvaleric acid are dissolved in 450 ml of absolute ethanol. 114 ml of concentrated sulphuric acid are added to the clear colourless solution and the reaction mixture is refluxed for 48 hours. The reaction mixture, which initially is two-phase, becomes almost homogeneous and separates into two phases again on cooling. The cold two-phase reaction mixture is poured onto diethyl ether and about 1 kg of ice. The aqueous phase is extracted with ether twice more. The ether phases are washed twice with 2 N sodium carbonate solution and twice with NaCl solution. The combined ether phases are dried over MgSO4 and the solvent is removed on a rotary evaporator. After drying under a high vacuum at room temperature, 281.7 g of a colourless oil (97.5% of theory) are obtained. the reaction mixture is refluxed for 48 hours on cooling The cold two-phase reaction mixture The aqueous phase is extracted with ether twice more The ether phases are washed twice with 2 N sodium carbonate solution and twice with NaCl solution The combined ether phases are dried over MgSO4 the solvent is removed on a rotary evaporator After drying under a high vacuum at room temperature

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

Procedure: 250 g (1.4 mols) of 5-phenylvaleric acid are dissolved in 450 ml of absolute ethanol. 114 ml of concentrated sulphuric acid are added to the clear colourless solution and the reaction mixture is refluxed for 48 hours. The reaction mixture, which initially is two-phase, becomes almost homogeneous and separates into two phases again on cooling. The cold two-phase reaction mixture is poured onto diethyl ether and about 1 kg of ice. The aqueous phase is extracted with ether twice more. The ether phases are washed twice with 2 N sodium carbonate solution and twice with NaCl solution. The combined ether phases are dried over MgSO4 and the solvent is removed on a rotary evaporator. After drying under a high vacuum at room temperature, 281.7 g of a colourless oil (97.5% of theory) are obtained. the reaction mixture is refluxed for 48 hours on cooling The cold two-phase reaction mixture The aqueous phase is extracted with ether twice more The ether phases are washed twice with 2 N sodium carbonate solution and twice with NaCl solution The combined ether phases are dried over MgSO4 the solvent is removed on a rotary evaporator After drying under a high vacuum at room temperature

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

Procedure: 250 g (1.4 mols) of 5-phenylvaleric acid are dissolved in 450 ml of absolute ethanol. 114 ml of concentrated sulphuric acid are added to the clear colourless solution and the reaction mixture is refluxed for 48 hours. The reaction mixture, which initially is two-phase, becomes almost homogeneous and separates into two phases again on cooling. The cold two-phase reaction mixture is poured onto diethyl ether and about 1 kg of ice. The aqueous phase is extracted with ether twice more. The ether phases are washed twice with 2 N sodium carbonate solution and twice with NaCl solution. The combined ether phases are dried over MgSO4 and the solvent is removed on a rotary evaporator. After drying under a high vacuum at room temperature, 281.7 g of a colourless oil (97.5% of theory) are obtained. the reaction mixture is refluxed for 48 hours on cooling The cold two-phase reaction mixture The aqueous phase is extracted with ether twice more The ether phases are washed twice with 2 N sodium carbonate solution and twice with NaCl solution The combined ether phases are dried over MgSO4 the solvent is removed on a rotary evaporator After drying under a high vacuum at room temperature

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

Procedure: 250 g (1.4 mols) of 5-phenylvaleric acid are dissolved in 450 ml of absolute ethanol. 114 ml of concentrated sulphuric acid are added to the clear colourless solution and the reaction mixture is refluxed for 48 hours. The reaction mixture, which initially is two-phase, becomes almost homogeneous and separates into two phases again on cooling. The cold two-phase reaction mixture is poured onto diethyl ether and about 1 kg of ice. The aqueous phase is extracted with ether twice more. The ether phases are washed twice with 2 N sodium carbonate solution and twice with NaCl solution. The combined ether phases are dried over MgSO4 and the solvent is removed on a rotary evaporator. After drying under a high vacuum at room temperature, 281.7 g of a colourless oil (97.5% of theory) are obtained. the reaction mixture is refluxed for 48 hours on cooling The cold two-phase reaction mixture The aqueous phase is extracted with ether twice more The ether phases are washed twice with 2 N sodium carbonate solution and twice with NaCl solution The combined ether phases are dried over MgSO4 the solvent is removed on a rotary evaporator After drying under a high vacuum at room temperature

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

Procedure: 250 g (1.4 moles) of 5-phenylvaleric acid are dissolved in 450 ml of absolute ethanol. 114 ml of concentrated sulphuric acid are added to the clear colourless solution and the reaction mixture is refluxed for 48 hours. The reaction mixture, which initially is two-phase, becomes almost homogeneous and separates into two phases again on cooling. The cold two-phase reaction mixture is poured onto diethyl ether and about 1 kg of ice. The aqueous phase is extracted with ether twice more. The ether phases are washed twice with 2 N sodium carbonate solution and twice with NaCl solution. The combined ether phases are dried over MgSO4 and the solvent is removed on a rotary evaporator. After drying under a high vacuum at room temperature, 281.7 g of a colourless oil (97.5% of theory) are obtained. the reaction mixture is refluxed for 48 hours on cooling The cold two-phase reaction mixture The aqueous phase is extracted with ether twice more The ether phases are washed twice with 2 N sodium carbonate solution and twice with NaCl solution The combined ether phases are dried over MgSO4 the solvent is removed on a rotary evaporator After drying under a high vacuum at room temperature

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

Procedure: 250 g (1.4 mols) of 5-phenylvaleric acid are dissolved in 450 ml of absolute ethanol. 114 ml of concentrated sulphuric acid are added to the clear colourless solution and the reaction mixture is refluxed for 48 hours. The reaction mixture, which initially is two-phase, becomes almost homogeneous and separates into two phases again on cooling. The cold two-phase reaction mixture is poured onto diethyl ether and about 1 kg of ice. The aqueous phase is extracted with ether twice more. The ether phases are washed twice with 2 N sodium carbonate solution and twice with NaCl solution. The combined ether phases are dried over MgSO4 and the solvent is removed on a rotary evaporator. After drying under a high vacuum at room temperature, 281.7 g of a colourless oil (97.5% of theory) are obtained. the reaction mixture is refluxed for 48 hours on cooling The cold two-phase reaction mixture The aqueous phase is extracted with ether twice more The ether phases are washed twice with 2 N sodium carbonate solution and twice with NaCl solution The combined ether phases are dried over MgSO4 the solvent is removed on a rotary evaporator After drying under a high vacuum at room temperature

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

Procedure: 47.9 g of 5-phenylvaleric acid ethyl ester are added to a sodium ethylate suspension, prepared from 6.4 g of sodium and 100 ml of ethanol with subsequent evaporation of excess ethanol and addition of 100 ml of toluene. 44.1 g of diethyl oxalate are added dropwise, whilst stirring, and the mixture is heated under reflux for 2.5 hours. After cooling, the solution is stirred with 500 ml of ice-water and the mixture is acidified to pH 2 with 2 N sulphuric acid. Extraction several times with methylene chloride gives, after drying, filtration through a short silica gel column and concentration, 62.1 g of 3-ethoxycarbonyl-2-oxo-6-phenylhexanoic acid ethyl ester, which is reacted according to (a), without further purification. the mixture is heated under reflux for 2.5 hours After cooling Extraction several times with methylene chloride gives after drying filtration through a short silica gel column and concentration, 62.1 g of 3-ethoxycarbonyl-2-oxo-6-phenylhexanoic acid ethyl ester, which is reacted according to (a), without further purification

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

Procedure: 250 g (1.4 mols) of 5-phenylvaleric acid are dissolved in 450 ml of absolute ethanol. 114 ml of concentrated sulphuric acid are added to the clear colourless solution and the reaction mixture is refluxed for 48 hours. The reaction mixture, which initially is two-phase, becomes almost homogeneous and separates into two phases again on cooling. The cold two-phase reaction mixture is poured onto diethyl ether and about 1 kg of ice. The aqueous phase is extracted with ether twice more. The ether phases are washed twice with 2 N sodium carbonate solution and twice with NaCl solution. The combined ether phases are dried over MgSO4 and the solvent is removed on a rotary evaporator. After drying under a high vacuum at room temperature, 281.7 g of a colourless oil (97.5% of theory) are obtained. the reaction mixture is refluxed for 48 hours on cooling The cold two-phase reaction mixture The aqueous phase is extracted with ether twice more The ether phases are washed twice with 2 N sodium carbonate solution and twice with NaCl solution The combined ether phases are dried over MgSO4 the solvent is removed on a rotary evaporator After drying under a high vacuum at room temperature

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

Procedure: 250 g (1.4 moles) of 5-phenylvaleric acid are dissolved in 450 ml of absolute ethanol. 114 ml of concentrated sulphuric acid are added to the clear colourless solution and the reaction mixture is refluxed for 48 hours. The reaction mixture, which initially is two-phase, becomes almost homogeneous and separates into two phases again on cooling. The cold two-phase reaction mixture is poured onto diethyl ether and about 1 kg of ice. The aqueous phase is extracted with ether twice more. The ether phases are washed twice with 2 N sodium carbonate solution and twice with NaCl solution. The combined ether phases are dried over MgSO4 and the solvent is removed on a rotary evaporator. After drying under a high vacuum at room temperature, 281.7 g of a colourless oil (97.5% of theory) are obtained. the reaction mixture is refluxed for 48 hours on cooling The cold two-phase reaction mixture The aqueous phase is extracted with ether twice more The ether phases are washed twice with 2 N sodium carbonate solution and twice with NaCl solution The combined ether phases are dried over MgSO4 the solvent is removed on a rotary evaporator After drying under a high vacuum at room temperature

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

Procedure: 250 g (1.4 mols) of 5-phenylvaleric acid are dissolved in 450 ml of absolute ethanol. 114 ml of concentrated sulphuric acid are added to the clear colourless solution and the reaction mixture is refluxed for 48 hours. The reaction mixture, which initially is two-phase, becomes almost homogeneous and separates into two phases again on cooling. The cold two-phase reaction mixture is poured onto diethyl ether and about 1 kg of ice. The aqueous phase is extracted with ether twice more. The ether phases are washed twice with 2 N sodium carbonate solution and twice with NaCl solution. The combined ether phases are dried over MgSO4 and the solvent is removed on a rotary evaporator. After drying under a high vacuum at room temperature, 281.7 g of a colourless oil (97.5% of theory) are obtained. the reaction mixture is refluxed for 48 hours on cooling The cold two-phase reaction mixture The aqueous phase is extracted with ether twice more The ether phases are washed twice with 2 N sodium carbonate solution and twice with NaCl solution The combined ether phases are dried over MgSO4 the solvent is removed on a rotary evaporator After drying under a high vacuum at room temperature