1-iodohexadecane

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Aniline (0.93 g), 1-iodohexadecane (10.56 g) and diisopropylethylamine (2.58 g) were combined in 10 ml of toluene. The mixture was heated at about 100° C. for a period of three days. The mixture was chromatographed on a silica gel column using 1% ethyl acetate in hexane. The heavy crystalline mass that precipitated from solution was cooled, diluted with ether and filtered. The filtrate was concentrated to an oil and applied to a silica gel column. The oil was washed with 500 ml of hexane followed by 1% ethyl acetate in hexane. The dialkylated fractions were combined and evaporated to give 2.6 grams of product. The mixture was chromatographed on a silica gel column The heavy crystalline mass that precipitated from solution was cooled diluted with ether filtered The filtrate was concentrated to an oil The oil was washed with 500 ml of hexane evaporated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 0° C. suspension, under argon, of 29 g of 60% sodium hydride in 350 ml of dimethylformamide is added dropwise over 40 minutes, 60.0 g of hydroquinone in 450 ml of dimethylformamide. The suspension is stirred at 0° C. for 1/2 hour; followed by the dropwise addition of 192 g of 1-iodohexadecane in 450 ml tetrahydrofuran. The reaction temperature is maintained at 0° C. during the addition of the alkyl halide; followed by stirring at room temperature for 3 hours. The mixture is poured carefully into dilute hydrochloric acid and extracted with chloroform. The organic layer is washed with water, dried and concentrated in vacuo. by stirring at room temperature for 3 hours extracted with chloroform The organic layer is washed with water dried concentrated in vacuo

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 0° C. suspension, under argon, of 29 g of 60% sodium hydride in 350 ml of dimethylformamide is added dropwise over 40 minutes, 60.0 g of hydroquinone in 450 ml of dimethylformamide. The suspension is stirred at 0° C. for 1/2 hour; followed by the dropwise addition of 192 g of 1-iodohexadecane in 450 ml tetrahydrofuran. The reaction temperature is maintained at 0° C. during the addition of the alkyl halide; followed by stirring at room temperature for 3 hours. The mixture is poured carefully into dilute hydrochloric acid and extracted with chloroform. The organic layer is washed with water, dried and concentrated in vacuo. by stirring at room temperature for 3 hours extracted with chloroform The organic layer is washed with water dried concentrated in vacuo

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

Procedure: To a refluxing solution of about 35.3 g of hexadecyl iodide in tetrahydrofuran was added a solution of about 37.4 g of bromoanisole and about 4.86 g of magnesium in tetrahydrofuran which had been refluxed for about 2 hours. An about 10 ml portion of about 0.1M lithium cupric chloride was added, the mixture was refluxed about 2 hours and stirred at room temperature for about 16 hours giving about 34 g of the desired reagent. had been refluxed for about 2 hours the mixture was refluxed about 2 hours

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of about 14.26 g of washed about 50% sodium hydride in about 500 ml of dimethylformamide was added about 49.2 g of 2-(benzyloxy)-1,3-propanediol over about 20 minutes. The mixture was stirred for about 40 minutes, then cooled to about 0° C. and about 95.13 g of hexadecyl iodide were added. After standing about 10 minutes, the mixture was stirred at room temperature for about 3 hours, then filtered through celite and diluted with about 1000 ml of water. This mixture was extracted with petroleum ether. The ether extract was dried and the solvent removed giving an oil. This oil was chromatographed on a column of florisil, eluting first with petroleum ether and then successively with about 5% and about 10% ether in petroleum ether to elute the product, giving about 28.8 g of the desired title compound as a light yellow oil. After standing about 10 minutes the mixture was stirred at room temperature for about 3 hours filtered through celite diluted with about 1000 ml of water This mixture was extracted with petroleum ether The ether extract was dried the solvent removed giving an oil This oil was chromatographed on a column of florisil eluting first with petroleum ether successively with about 5% and about 10% ether in petroleum ether to elute the product

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of 28.99 g of 60% sodium hydride in 350 ml of N,N-dimethylformamide, cooled to 0° C. and under argon is added 60 g of hydroquinone in 450 ml of N,N-dimethylformamide with stirring over 40 minutes. After an additional 30 minutes, 450 ml of tetrahydrofuran is added followed by 192 g of 1-iodohexadecane over one hour. The mixture is stirred at room temperature for 3 hours. The reaction mixture is poured into dilute hydrochloric acid and extracted with chloroform. The organic layer is washed with water, dried and evaporated to give the desired product as an oil. After an additional 30 minutes The mixture is stirred at room temperature for 3 hours extracted with chloroform The organic layer is washed with water dried evaporated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of 28.99 g of 60% sodium hydride in 350 ml of N,N-dimethylformamide, cooled to 0° C. and under argon is added 60 g of hydroquinone in 450 ml of N,N-dimethylformamide with stirring over 40 minutes. After an additional 30 minutes, 450 ml of tetrahydrofuran is added followed by 192 g of 1-iodohexadecane over one hour. The mixture is stirred at room temperature for 3 hours. The reaction mixture is poured into dilute hydrochloric acid and extracted with chloroform. The organic layer is washed with water, dried and evaporated to give the desired product as an oil. After an additional 30 minutes The mixture is stirred at room temperature for 3 hours extracted with chloroform The organic layer is washed with water dried evaporated

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,8-Diazabicyclo[5.4.0]undec-7-ene(1,5-5)(4.567 g, 30 mmol) was added at room temperature to a solution of citric acid (1.924 g, 10 mmol) in N,N-dimethylformamide (50 ml). 1-Iodohexadecane (10.570 g, 30 mmol) was added and the resulting mixture was stirred at 50° C. for 21 hours. The precipitated product was filtered off and washed with N,N-dimethylformamide and the crude product was purified by flash chromatography on silica gel using chlorform/hexane for elution. Yield: 83%. 1H-NMR (300 MHz, CDCl3): δ 088(t,9H), 1.26(m,78H), 1.60(m,6H), 2.84(q,4H), 4.07(t,4H), 4.13(s,1H), 4.20(t,2H). FAB-MS: 887.6(M+Na). The precipitated product was filtered off washed with N,N-dimethylformamide the crude product was purified by flash chromatography on silica gel for elution

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

Procedure: Sodium hydride (72 mg, 3 mmol) was added in portions to a cooled (ice/water) solution of 2-hexadecylmalonic acid dihexadecyl ester (2.33 g, 3 mmol) in tetrahydrofuran (45 ml) under an argon atmosphere and the resulting mixture was stirred at ambient temperature for 30 minutes. The solvent was evaporated and the solid residue was redissolved in N,N-dimethylformamide (45 ml). A solution of 1-iodohexadecane (1.06 g, 3 mmol) in N,N-dimethylformamide (20 ml) was added and stirring was continued at room temperature for 24 hours. Water (75 ml) was added to the reaction mixture after the pH had been adjusted to about 5 with 2N HCl. The mixture was extracted with chloroform (3×75 ml) and the chloroform phase was washed with water (3×75 ml). The organic phase was dried with magnesium sulphate and the solvent was removed at reduced pressure. The residue was purified by flash chromatography (silicagel 60, chloroform/hexane). Yield: 66%. 1H-NMR (300 MHz, CDCl3): δ 0.88(t,12H), 1.26(m,108H), 1.60(m,4H), 1.85(m,4H), 4.09(t,4H). FAB-MS: 1024 (M+Na). The solvent was evaporated the solid residue was redissolved in N,N-dimethylformamide (45 ml) stirring was continued at room temperature for 24 hours The mixture was extracted with chloroform (3×75 ml) the chloroform phase was washed with water (3×75 ml) The organic phase was dried with magnesium sulphate the solvent was removed at reduced pressure The residue was purified by flash chromatography (silicagel 60, chloroform/hexane)

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

Procedure: Sodium hydride (72 mg, 3 mmol) was added in portions to a cooled (ice/water) solution of 2-hexadecylmalonic acid dihexadecyl ester (2.33 g, 3 mmol) in tetrahydrofuran (45 ml) under an argon atmosphere and the resulting mixture was stirred at ambient temperature for 30 minutes. The solvent was evaporated and the solid residue was redissolved in N,N-dimethylformamide (45 ml). A solution of 1-iodohexadecane (1.06 g, 3 mmol) in N,N-dimethylformamide (20 ml) was added and stirring was continued at room temperature for 24 hours. Water (75 ml) was added to the reaction mixture after the pH had been adjusted to about 5 with 2N HCl. The mixture was extracted with chloroform (3×75 ml) and the chloroform phase was washed with water (3×75 ml). The organic phase was dried with magnesium sulphate and the solvent was removed at reduced pressure. The residue was purified by flash chromatography (silicagel 60, chloroform/hexane). Yield: 66%. 1H-NMR (300 MHz, CDCl3): δ 0.88(t,12H), 1.26(m,108H), 1.60(m,4H), 1.85(m,4H), 4.09(t,4H). FAB-MS: 1024 (M+Na). The solvent was evaporated the solid residue was redissolved in N,N-dimethylformamide (45 ml) stirring was continued at room temperature for 24 hours The mixture was extracted with chloroform (3×75 ml) the chloroform phase was washed with water (3×75 ml) The organic phase was dried with magnesium sulphate the solvent was removed at reduced pressure The residue was purified by flash chromatography (silicagel 60, chloroform/hexane)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of 28.99 g of 60% sodium hydride in 350 ml of N,N-dimethylformamide, cooled to 0° C. and under argon is added 60 g of hydroquinone in 450 ml of N,N-dimethylformamide with stirring over 40 minutes. After an additional 30 minutes, 450 ml of tetrahydrofuran is added followed by 192 g of 1-iodohexadecane over one hour. The mixture is stirred at room temperature for 3 hours. The reaction mixture is poured into dilute hydrochloric acid and extracted with chloroform. The organic layer is washed with water, dried and evaporated to give the desired product as an oil. After an additional 30 minutes The mixture is stirred at room temperature for 3 hours extracted with chloroform The organic layer is washed with water dried evaporated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of 28.99 g of 60% sodium hydride in 350 ml of N,N-dimethylformamide, cooled to 0° C. and under argon is added 60 g of hydroquinone in 450 ml of N,N-dimethylformamide with stirring over 40 minutes. After an additional 30 minutes, 450 ml of tetrahydrofuran is added followed by 192 g of 1-iodohexadecane over one hour. The mixture is stirred at room temperature for 3 hours. The reaction mixture is poured into dilute hydrochloric acid and extracted with chloroform. The organic layer is washed with water, dried and evaporated to give the desired product as an oil. After an additional 30 minutes The mixture is stirred at room temperature for 3 hours extracted with chloroform The organic layer is washed with water dried evaporated