1-[4-(2-hydroxyethyl)phenyl]octan-1-one

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: 4′-(2-Hydroxy ethyl)octanophenone prepared in the step B (137 g), imidazole (53 g) and triphenyl phosphine (174 g) were dissolved in ethyl acetate (550 ml) to obtain a solution. Iodine (197 g) was added to the solution with cooling, and the solution was stirred at room temperature for 1 hour. Then the reaction solution was diluted with ethyl acetate, the solution was washed with saturated sodium sulfite solution, and saturated saline solution, dried over anhydrous magnesium sulfate, and concentrated. The concentrated residue was extracted with hexane-ethyl acetate (20:1), and extracted solution was passed through a silica gel layer. The filtrate was concentrated to obtain 4′-(2-iodoethyl)octanophenone (175 g) in the form of white crystal. to obtain a solution with cooling the solution was washed with saturated sodium sulfite solution, and saturated saline solution dried over anhydrous magnesium sulfate concentrated The concentrated residue was extracted with hexane-ethyl acetate (20:1) extracted solution The filtrate was concentrated

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

Procedure: A solution (18.8 ml) of 28% sodium methylate in methanol was added to a solution of the material (280 g) which contains 2-(4-octanoyl phenyl)ethyl acetate obtained in the step A as a major component in methanol (200 ml), and the solution was stirred at room temperature for 1 hour. Suspension of Amberlite IR-120B in methanol (98 ml) was added to the solution, and the mixture was filtered. The filtrate was concentrated, and the residue was recrystallized from hexane-ethyl acetate (10:1) to obtain 4′-(2-hydroxy ethyl)octanophenone (138 g) in the form of colorless crystal. was added to the solution the mixture was filtered The filtrate was concentrated the residue was recrystallized from hexane-ethyl acetate (10:1)

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

Procedure: 4′-(2-Hydroxy ethyl)octanophenone (1.0 g) prepared in the step B was dissolved in dichloromethane (10 ml) to obtain a solution. p-Toluene sulfonyl chloride (923 mg) and pyridine (383 mg) were added to the solution with cooling, and the mixture was stirred at room temperature for 2 hours. After the reaction, ice water was added to the solution, the solution was stirred at room temperature for 20 minutes. Dichloromethane layer was washed with 2% hydrochloric acid, sodium bicarbonate solution, and water. The dichloromethane layer was dried over anhydrous sodium sulfate, and concentrated. The residue was recrystallized from hexane-ethyl acetate (10:1) to obtain 2-(4-octanoyl phenyl)ethyl p-toluene sulfonate (950 mg) in the form of colorless crystal. to obtain a solution with cooling was added to the solution the solution was stirred at room temperature for 20 minutes Dichloromethane layer was washed with 2% hydrochloric acid, sodium bicarbonate solution, and water The dichloromethane layer was dried over anhydrous sodium sulfate concentrated The residue was recrystallized from hexane-ethyl acetate (10:1)