4-chlorobutylbenzene

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:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium iodide (8.9 g, 59.2 mol) and 4-phenyl-1-chlorobutane (5.0 g, 29.6 mol) were added to acetone (29.6 mL) at rt. The mixture was heated to 70° C. for 12 h. The resulting solution was gravity filtered to remove salts. The solvent was removed under reduced pressure and excess salts were dissolved in water (100 mL). Hexane (100 mL) was added to the aqueous mixture. The phases were separated and the organic phase was washed with saturated sodium bisulfite solution (3×50 mL), treated with decolorizing carbon, and gravity filtered. The organic layer was then dried (MgSO4), filtered, and concentrated in vacuo to afford 4-phenyl-1-iodobutane (6.94 g, 90%). filtered to remove salts The solvent was removed under reduced pressure and excess salts were dissolved in water (100 mL) Hexane (100 mL) was added to the aqueous mixture The phases were separated the organic phase was washed with saturated sodium bisulfite solution (3×50 mL) treated with decolorizing carbon, and gravity filtered The organic layer was then dried (MgSO4) filtered concentrated in vacuo

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

Procedure: 1,2,3-Triazole (1623 mg, 23.5 mmol), sodium iodide (2353 mg, 15.7 mmol) and sodium hydroxide (940 mg, 23.5 mmol) were added to t-amyl alcohol (6.2 ml), and the mixture was refluxed under stirring for 1 hour. 1-Chloro-4-phenylbutane (2648 mg, 15.7 mmol) was dissolved in t-amyl alcohol (6.2 ml) and added dropwise under reflux over 1 hour. The mixture was refluxed under stirring for 2 hours and cooled to room temperature, and toluene (50 ml) was added. The mixture was washed with water (50 ml×2), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1→1/3) to give 1-(4-phenylbutyl)-1H-1,2,3-triazole (2.56 g) as colorless oil. yield 81%. 2-(4-Phenylbutyl)-2H-1,2,3-triazole (360 mg) was obtained as a colorless oil (yield 11%). 1-(4-phenylbutyl)-1H-1,2,3-triazole the mixture was refluxed added dropwise under reflux over 1 hour The mixture was refluxed under stirring for 2 hours The mixture was washed with water (50 ml×2) dried over anhydrous sodium sulfate concentrated under reduced pressure The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1→1/3)

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium iodide (8.9 g, 59.2 mol) and 4-phenyl-1-chlorobutane (5.0 g, 29.6 mol) were added to acetone (29.6 mL) at rt. The mixture was heated to 70° C. for 12 h. The resulting solution was gravity filtered to remove salts. The solvent was removed under reduced pressure and excess salts were dissolved in water (100 mL). Hexane (100 mL) was added to the aqueous mixture. The phases were separated and the organic phase was washed with saturated sodium bisulfite solution (3×50 mL), treated with decolorizing carbon, and gravity filtered. The organic layer was then dried (MgSO4), filtered, and concentrated in vacuo to afford 4-phenyl-1 -iodobutane (6.94 g, 90%). filtered to remove salts The solvent was removed under reduced pressure and excess salts were dissolved in water (100 mL) Hexane (100 mL) was added to the aqueous mixture The phases were separated the organic phase was washed with saturated sodium bisulfite solution (3×50 mL) treated with decolorizing carbon, and gravity filtered The organic layer was then dried (MgSO4) filtered concentrated in vacuo

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium iodide (8.9 g, 59.2 mol) and 4-phenyl-1-chlorobutane (5.0 g, 29.6 mol) were added to acetone (29.6 mL) at rt. The mixture was heated to 70° C. for 12 h. The resulting solution was gravity filtered to remove salts. The solvent was removed under reduced pressure and excess salts were dissolved in water (100 mL). Hexane (100 mL) was added to the aqueous mixture. The phases were separated and the organic phase was washed with saturated sodium bisulfite solution (3×50 mL), treated with decolorizing carbon, and gravity filtered. The organic layer was then dried (MgSO4), filtered, and concentrated in vacuo to afford 4-phenyl-1-iodobutane (6.94 g, 90%). filtered to remove salts The solvent was removed under reduced pressure and excess salts were dissolved in water (100 mL) Hexane (100 mL) was added to the aqueous mixture The phases were separated the organic phase was washed with saturated sodium bisulfite solution (3×50 mL) treated with decolorizing carbon, and gravity filtered The organic layer was then dried (MgSO4) filtered concentrated in vacuo

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium iodide (8.9 g, 59.2 mol) and 4-phenyl-1-chlorobutane (5.0 g, 29.6 mol) were added to acetone (29.6 mL) at rt. The mixture was heated to 70° C. for 12 h. The resulting solution was gravity filtered to remove salts. The solvent was removed under reduced pressure and excess salts were dissolved in water (100 mL). Hexane (100 mL) was added to the aqueous mixture. The phases were separated and the organic phase was washed with saturated sodium bisulfite solution (3×50 mL), treated with decolorizing carbon, and gravity filtered. The organic layer was then dried (MgSO4), filtered, and concentrated in vacuo to afford 4-phenyl-1-iodobutane (6.94 g, 90%). filtered to remove salts The solvent was removed under reduced pressure and excess salts were dissolved in water (100 mL) Hexane (100 mL) was added to the aqueous mixture The phases were separated the organic phase was washed with saturated sodium bisulfite solution (3×50 mL) treated with decolorizing carbon, and gravity filtered The organic layer was then dried (MgSO4) filtered concentrated in vacuo

Conditions: temp:185.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4-phenylbutyl chloride (8.0 g, 47.5 mmole) and triethylphosphite (15.0 ml, 72 mmole) was heated at reflux (bath temperature 185° C.) under argon for 41.5 hours. Distillation of the mixture gave pure diethyl (4-phenylbutyl)phosphonate (10.8 g, 84%) as a colorless liquid, b.p. 152°-154° C. (1.0 mmHg). TLC (EtOAc) single spot Rf =0.55. was heated Distillation of the mixture

Conditions: temp:185.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4-phenylbutyl chloride (8.0 g, 47.5 mmole) and triethylphosphite (15.0 ml, 72 mmole) was heated at reflux (bath temperature 185° C.) under argon for 41.5 hours. Distillation of the mixture gave pure diethyl (4-phenylbutyl)phosphonate (10.8 g, 84%) as a colorless liquid, b.p. 152°-154° C. (1.0 mmHg). TLC (EtOAc) single spot Rf =0.55. was heated Distillation of the mixture

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

Procedure: A 2.2 ml (20 mmol) amount of thionyl chloride was added dropwise to a methylene chloride solution (30 ml) containing 3 g (20 mmol) of 4-phenyl-1-butanol and stirred overnight at room temperature. The reaction solution was washed with water, an aqueous 50% sodium hydrogen carbonate solution, water, 1N hydrochloric acid and water in that order, and then the solvent was dried with anhydrous magnesium sulfate. After distillation under reduced pressure, 3.62 g of a crude 4-phenylbutyl chloride was obtained. This material was used in the next reaction without being further purified. The reaction solution was washed with water an aqueous 50% sodium hydrogen carbonate solution, water, 1N hydrochloric acid and water in that order, and then the solvent was dried with anhydrous magnesium sulfate After distillation under reduced pressure

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium iodide (8.9 g, 59.2 mol) and 4-phenyl-1-chlorobutane (5.0 g, 29.6 mol) were added to acetone (29.6 mL) at rt. The mixture was heated to 70° C. for 12 h. The resulting solution was gravity filtered to remove salts. The solvent was removed under reduced pressure and excess salts were dissolved in water (100 mL). Hexane (100 mL) was added to the aqueous mixture. The phases were separated and the organic phase was washed with saturated sodium bisulfite solution (3×50 mL), treated with decolorizing carbon, and gravity filtered. The organic layer was then dried (MgSO4), filtered, and concentrated in vacuo to afford 4-phenyl-1-iodobutane (6.94 g, 90%). filtered to remove salts The solvent was removed under reduced pressure and excess salts were dissolved in water (100 mL) Hexane (100 mL) was added to the aqueous mixture The phases were separated the organic phase was washed with saturated sodium bisulfite solution (3×50 mL) treated with decolorizing carbon, and gravity filtered The organic layer was then dried (MgSO4) filtered concentrated in vacuo