1-(chloromethyl)-4-propylbenzene

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

Procedure: (4-Propylphenyl)methanol (4.93 g) synthesized in Reference Example 36 was dissolved in carbon tetrachloride (65 mL), triphenylphosphine (9.5 g) was added thereto, and the mixture was heated under reflux for 4 hr. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in hexane. The insoluble material was filtered off, and the filtrate was evaporated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent; hexane) to give the title compound (2.24 g) as a colorless oil. the mixture was heated under reflux for 4 hr The reaction mixture was concentrated under reduced pressure the residue was dissolved in hexane The insoluble material was filtered off the filtrate was evaporated under reduced pressure The residue was purified by silica gel chromatography (elution solvent; hexane)

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

Procedure: In 50 ml of chloroform was dissolved 8.63 g (57.5 mmol) of 4-n-propylbenzyl alcohol synthesized in the step (ii), and 8.10 g (68.1 mmol) of thionyl chloride was added to the mixture. The mixture was subjected to reaction at a room temperature for 24 hours. After the completion of the reaction, the chloroform phase was washed successively with an aqueous solution of sodium hydrogencarbonate and water. Chloroform was removed from the chloroform phase to give 9.40 g (55.8 mmol) of 4-n-propylbenzylchloride. was added to the mixture The mixture was subjected to reaction at a room temperature for 24 hours After the completion of the reaction the chloroform phase was washed successively with an aqueous solution of sodium hydrogencarbonate and water Chloroform was removed from the chloroform phase

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

Procedure: (4-Propylphenyl)methanol (4.93 g) synthesized in Reference Example 36 was dissolved in carbon tetrachloride (65 mL), triphenylphosphine (9.5 g) was added thereto, and the mixture was heated under reflux for 4 hr. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in hexane. The insoluble material was filtered off, and the filtrate was evaporated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent; hexane) to give the title compound (2.24 g) as a colorless oil. the mixture was heated under reflux for 4 hr The reaction mixture was concentrated under reduced pressure the residue was dissolved in hexane The insoluble material was filtered off the filtrate was evaporated under reduced pressure The residue was purified by silica gel chromatography (elution solvent; hexane)

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

Procedure: In 50 ml of chloroform was dissolved 8.63 g (57.5 mmol) of 4-n-propylbenzyl alcohol synthesized in the step (ii), and 8.10 g (68.1 mmol) of thionyl chloride was added to the mixture. The mixture was subjected to reaction at a room temperature for 24 hours. After the completion of the reaction, the chloroform phase was washed successively with an aqueous solution of sodium hydrogencarbonate and water. Chloroform was removed from the chloroform phase to give 9.40 g (55.8 mmol) of 4-n-propylbenzylchloride. was added to the mixture The mixture was subjected to reaction at a room temperature for 24 hours After the completion of the reaction the chloroform phase was washed successively with an aqueous solution of sodium hydrogencarbonate and water Chloroform was removed from the chloroform phase