2-(3-phenylpropyl)phenol

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

Procedure: The whole of this benzyl 2-(3-phenyl-1-propenyl)phenyl ether was treated with hydrogen in the presence of 100 mg of 5% w/w palladium-on-carbon in 40 ml of ethanol at room temperature for 3 hours. At the end of this time, insoluble materials were removed by filtration, and the filtrate was concentrated by distillation under reduced pressure, to give 0.230 g (yield 83%) of the title compound as a colorless oil. At the end of this time, insoluble materials were removed by filtration the filtrate was concentrated by distillation under reduced pressure

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

Procedure: 134 mg of 3-(N,N-dimethylamino)propanol and 342 mg of triphenyl phosphine were added to a solution of 230 mg of 2-(3-phenylpropyl)phenol (prepared as described in Preparation 29) in 10 ml of methylene chloride, and the mixture was cooled with ice and stirred. 227 mg of diethyl azodicarboxylate were then added dropwise to the solution, and the mixture was stirred at room temperature for 5 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and ethyl acetate and water were added to the residue and shaken. The ethyl acetate layer was separated and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a 10:1 by volume mixture of methylene chloride and methanol as the eluent, to give 115 mg (yield 36%) of the title compound as a colorless oil. the mixture was cooled with ice the mixture was stirred at room temperature for 5 hours At the end of this time, the solvent was removed by distillation under reduced pressure, and ethyl acetate and water were added to the residue shaken The ethyl acetate layer was separated dried over anhydrous magnesium sulfate The solvent was then removed by distillation under reduced pressure the resulting residue was purified by column chromatography through silica gel by volume mixture of methylene chloride and methanol as the eluent

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

Procedure: 134 mg of 3-(N,N-dimethylamino)propanol and 342 mg of triphenyl phosphine were added to a solution of 230 mg of 2-(3-phenylpropyl)phenol (prepared as described in Preparation 29) in 10 ml of methylene chloride, and the mixture was cooled with ice and stirred. 227 mg of diethyl azodicarboxylate were then added dropwise to the solution, and the mixture was stirred at room temperature for 5 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and ethyl acetate and water were added to the residue and shaken. The ethyl acetate layer was separated and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a 10:1 by volume mixture of methylene chloride and methanol as the eluent, to give 115 mg (yield 36%) of the title compound as a colorless oil. the mixture was cooled with ice the mixture was stirred at room temperature for 5 hours At the end of this time, the solvent was removed by distillation under reduced pressure, and ethyl acetate and water were added to the residue shaken The ethyl acetate layer was separated dried over anhydrous magnesium sulfate The solvent was then removed by distillation under reduced pressure the resulting residue was purified by column chromatography through silica gel by volume mixture of methylene chloride and methanol as the eluent

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

Procedure: The whole of this benzyl 2-(3-phenyl-1-propenyl)phenyl ether was treated with hydrogen in the presence of 100 mg of 5% w/w palladium-on-carbon in 40 ml of ethanol at room temperature for 3 hours. At the end of this time, insoluble materials were removed by filtration, and the filtrate was concentrated by distillation under reduced pressure, to give 0.230 g (yield 83%) of the title compound as a colorless oil. At the end of this time, insoluble materials were removed by filtration the filtrate was concentrated by distillation under reduced pressure

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

Procedure: 134 mg of 3-(N,N-dimethylamino)propanol and 342 mg of triphenyl phosphine were added to a solution of 230 mg of 2-(3-phenylpropyl)phenol (prepared as described in Preparation 29) in 10 ml of methylene chloride, and the mixture was cooled with ice and stirred. 227 mg of diethyl azodicarboxylate were then added dropwise to the solution, and the mixture was stirred at room temperature for 5 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and ethyl acetate and water were added to the residue and shaken. The ethyl acetate layer was separated and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a 10:1 by volume mixture of methylene chloride and methanol as the eluent, to give 115 mg (yield 36%) of the title compound as a colorless oil. the mixture was cooled with ice the mixture was stirred at room temperature for 5 hours At the end of this time, the solvent was removed by distillation under reduced pressure, and ethyl acetate and water were added to the residue shaken The ethyl acetate layer was separated dried over anhydrous magnesium sulfate The solvent was then removed by distillation under reduced pressure the resulting residue was purified by column chromatography through silica gel by volume mixture of methylene chloride and methanol as the eluent