8-chlorooctylbenzene

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

Procedure: A suspension of 8-phenyloctyl chloride (10.1 g, 44.7 mmol), benzylamine (47.9 g, 44.7 mmol), and anhydrous powdered potassium carbonate in DMF (180 ml) refluxed overnight and cooled to RT. DMF was then evaporated under reduced pressure and water (300 ml) was added to the residue. The oil layer was separated, and the aqueous layer was further extracted with ether (2×150 ml). The ether extracts were evaporated and then combined with the oil layer. The combined oil was diluted with water (250 ml) and acidified with 10% HCl solution to give a white precipitate, 16 g, which was suspended in water (150 ml) and basified with ammonium hydroxide. After being stirred for 10 minutes, most of the white solid went into the solution. Ether (100 ml) was added and stirred for an additional 30 minutes. Organic layer was separated and the aqueous layer was extracted with ether (150 ml×2). Ether extracts were combined, washed with water and saturated brine solution, and dried (MgSO4), thus giving a light yellow oil of 11.90 g (90% yield). refluxed overnight DMF was then evaporated under reduced pressure and water (300 ml) was added to the residue The oil layer was separated the aqueous layer was further extracted with ether (2×150 ml) The ether extracts were evaporated The combined oil was diluted with water (250 ml) to give a white precipitate, 16 g, which stirred for an additional 30 minutes Organic layer was separated the aqueous layer was extracted with ether (150 ml×2) washed with water and saturated brine solution dried (MgSO4) thus giving a light yellow oil of 11.90 g (90% yield)

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

Procedure: A mixture of 8-phenyloctyl chloride (4.4 g), sodium iodide (5.34 g) and acetone (20 ml) was heated under reflux for 20 hours. Evaporated, water (20 ml) added and extracted with diethyl ether (20 ml). The extracts were dried, filtered and evaporated to a pale yellow liquid (5.5 g). Distilled to give 8-phenyloctyl iodide, b.p. 200° C. (air bath temperature) at 0.1 mBar. was heated under reflux for 20 hours Evaporated water (20 ml) added extracted with diethyl ether (20 ml) The extracts were dried filtered evaporated to a pale yellow liquid (5.5 g) Distilled

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

Procedure: A mixture of 8-phenyloctyl chloride (4.4 g), sodium iodide (5.34 g) and acetone (20 ml) was heated under reflux for 20 hours. Evaporated, water (20 ml) added and extracted with diethyl ether (20 ml). The extracts were dried, filtered and evaporated to a pale yellow liquid (5.5 g). Distilled to give 8-phenyloctyl iodide, b.p. 200° C. (air bath temperature) at 0.1 mBar. was heated under reflux for 20 hours Evaporated water (20 ml) added extracted with diethyl ether (20 ml) The extracts were dried filtered evaporated to a pale yellow liquid (5.5 g) Distilled

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 14.9 g. of ethyl p-aminobenzoate, 50 ml. of hexamethylphosphoramide, 10.1 g. of 8-phenyloctyl chloride and 6.75 g. of sodium iodide is stirred and heated in an oil bath at 110° C. for 24 hours. The mixture is chilled, diluted with 50 ml. of water and 25 ml. of ethanol, chilled and filtered. The solid is washed with ethanol-water (1:1) and with water to give crystals, m.p. 61°-68° C. Recrystallization from ethanol gives white crystals, m.p. 75°-76° C. A mixture of 14.9 g The mixture is chilled diluted with 50 ml filtered The solid is washed with ethanol-water (1:1) and with water to give crystals, m.p. 61°-68° C Recrystallization from ethanol gives white crystals, m.p. 75°-76° C.

Conditions: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 14.9 g. of ethyl p-aminobenzoate, 50 ml. of hexamethylphosphoramide, 10.1 g. of 8-phenyloctyl chloride and 6.75 g. of sodium iodide is stirred and heated in an oil bath at 110° C. for 24 hours. The mixture is chilled, diluted with 50 ml. of water and 25 ml. of ethanol, chilled and filtered. The solid is washed with ethanol-water (1:1) and with water to give crystals, m.p. 61°-68° C. Recrystallization from ethanol gives white crystals, m.p. 75°-76° C. A mixture of 14.9 g The mixture is chilled diluted with 50 ml filtered The solid is washed with ethanol-water (1:1) and with water to give crystals, m.p. 61°-68° C Recrystallization from ethanol gives white crystals, m.p. 75°-76° C.

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

Procedure: A suspension of 8-phenyloctyl chloride (10.1 g, 44.7 mmol), benzylamine (47.9 g, 44.7 mmol), and anhydrous powdered potassium carbonate in DMF (180 ml) refluxed overnight and cooled to RT. DMF was then evaporated under reduced pressure and water (300 ml) was added to the residue. The oil layer was separated, and the aqueous layer was further extracted with ether (2×150 ml). The ether extracts were evaporated and then combined with the oil layer. The combined oil was diluted with water (250 ml) and acidified with 10% HCl solution to give a white precipitate, 16 g, which was suspended in water (150 ml) and basified with ammonium hydroxide. After being stirred for 10 minutes, most of the white solid went into the solution. Ether (100 ml) was added and stirred for an additional 30 minutes. Organic layer was separated and the aqueous layer was extracted with ether (150 ml×2). Ether extracts were combined, washed with water and saturated brine solution, and dried (MgSO4), thus giving a light yellow oil of 11.90 g (90% yield). refluxed overnight DMF was then evaporated under reduced pressure and water (300 ml) was added to the residue The oil layer was separated the aqueous layer was further extracted with ether (2×150 ml) The ether extracts were evaporated The combined oil was diluted with water (250 ml) to give a white precipitate, 16 g, which stirred for an additional 30 minutes Organic layer was separated the aqueous layer was extracted with ether (150 ml×2) washed with water and saturated brine solution dried (MgSO4) thus giving a light yellow oil of 11.90 g (90% yield)

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

Procedure: A mixture of 8-phenyloctyl chloride (4.4 g), sodium iodide (5.34 g) and acetone (20 ml) was heated under reflux for 20 hours. Evaporated, water (20 ml) added and extracted with diethyl ether (20 ml). The extracts were dried, filtered and evaporated to a pale yellow liquid (5.5 g). Distilled to give 8-phenyloctyl iodide, b.p. 200° C. (air bath temperature) at 0.1 mBar. was heated under reflux for 20 hours Evaporated water (20 ml) added extracted with diethyl ether (20 ml) The extracts were dried filtered evaporated to a pale yellow liquid (5.5 g) Distilled