1-pentoxypentane

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

Procedure: At a temperature of -78° C., 19.4 ml of t-butyl lithium (1.7M) is added to 4.0 gm of the above 3-bromo-phenol, n-pentyl ether in 50 mls tetrahydrofuran; and to this is added 3.3 ml of a freshly prepared solution of Li2CuCl3 (0.10M/THF). The mixture is stirred for 10 minutes, and then 4.35 grams of the 1-bromo-5-benzyloxy pentane are added. The reaction is allowed to warm slowly to ambient temperature over 12 hours and is then stirred an additional 24 hours before being quenched with silica gel. After removing the solvent, the mixture is chromatographed over silica gel (1:1 hexane:ether) to yield a crude mixture containing 3-(benzyloxypentyl)-phenol, n-pentyl ether. A solution of 6.0 gm of this crude mixture in ethanol is hydrogenated over 5% Pd on carbon for 5 hours. After filtering through celite and concentrating, pure 3-(5-hydroxypentyl)-phenol, n-pentyl ether is obtained as a clear oil by HPLC chromatography. is then stirred an additional 24 hours before being quenched with silica gel After removing the solvent the mixture is chromatographed over silica gel (1:1 hexane:ether) to yield a crude mixture After filtering through celite concentrating

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 5.0 gm of 3-Bromophenol in 60 mls of dimethylformamide is added 6.0 gm of potassium carbonate followed by 4.3 ml of 1-bromopentane. This mixture is heated to 60° C. for 6 hours and then cooled to room temperature and filtered. The filtrate is diluted with ether and washed with water and brine. After drying over magnesium sulfate and concentrating, the crude oil obtained is chromatographed over silica gel, and eluted with 3:2 hexane:ether to yield 3-bromo-phenol, n-pentyl ether as a clear oil. cooled to room temperature filtered The filtrate is diluted with ether washed with water and brine After drying over magnesium sulfate concentrating the crude oil obtained is chromatographed over silica gel eluted with 3:2 hexane

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

Procedure: At a temperature of -78° C., 19.4 ml of t-butyl lithium (1.7M) is added to 4.0 gm of the above 3-bromo-phenol, n-pentyl ether in 50 mls tetrahydrofuran; and to this is added 3.3 ml of a freshly prepared solution of Li2CuCl3 (0.10M/THF). The mixture is stirred for 10 minutes, and then 4.35 grams of the 1-bromo-5-benzyloxy pentane are added. The reaction is allowed to warm slowly to ambient temperature over 12 hours and is then stirred an additional 24 hours before being quenched with silica gel. After removing the solvent, the mixture is chromatographed over silica gel (1:1 hexane:ether) to yield a crude mixture containing 3-(benzyloxypentyl)-phenol, n-pentyl ether. A solution of 6.0 gm of this crude mixture in ethanol is hydrogenated over 5% Pd on carbon for 5 hours. After filtering through celite and concentrating, pure 3-(5-hydroxypentyl)-phenol, n-pentyl ether is obtained as a clear oil by HPLC chromatography. is then stirred an additional 24 hours before being quenched with silica gel After removing the solvent the mixture is chromatographed over silica gel (1:1 hexane:ether) to yield a crude mixture After filtering through celite concentrating

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 5.0 gm of 3-Bromophenol in 60 mls of dimethylformamide is added 6.0 gm of potassium carbonate followed by 4.3 ml of 1-bromopentane. This mixture is heated to 60° C. for 6 hours and then cooled to room temperature and filtered. The filtrate is diluted with ether and washed with water and brine. After drying over magnesium sulfate and concentrating, the crude oil obtained is chromatographed over silica gel, and eluted with 3:2 hexane:ether to yield 3-bromo-phenol, n-pentyl ether as a clear oil. cooled to room temperature filtered The filtrate is diluted with ether washed with water and brine After drying over magnesium sulfate concentrating the crude oil obtained is chromatographed over silica gel eluted with 3:2 hexane

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 5.0 gm of 3-Bromophenol in 60 mls of dimethylformamide is added 6.0 gm of potassium carbonate followed by 4.3 ml of 1-bromopentane. This mixture is heated to 60° C. for 6 hours and then cooled to room temperature and filtered. The filtrate is diluted with ether and washed with water and brine. After drying over magnesium sulfate and concentrating, the crude oil obtained is chromatographed over silica gel, and eluted with 3:2 hexane:ether to yield 3-bromo-phenol, n-pentyl ether as a clear oil. cooled to room temperature filtered The filtrate is diluted with ether washed with water and brine After drying over magnesium sulfate concentrating the crude oil obtained is chromatographed over silica gel eluted with 3:2 hexane

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

Procedure: At a temperature of -78° C., 19.4 ml of t-butyl lithium (1.7M) is added to 4.0 gm of the above 3-bromo-phenol, n-pentyl ether in 50 mls tetrahydrofuran; and to this is added 3.3 ml of a freshly prepared solution of Li2CuCl3 (0.10M/THF). The mixture is stirred for 10 minutes, and then 4.35 grams of the 1-bromo-5-benzyloxy pentane are added. The reaction is allowed to warm slowly to ambient temperature over 12 hours and is then stirred an additional 24 hours before being quenched with silica gel. After removing the solvent, the mixture is chromatographed over silica gel (1:1 hexane:ether) to yield a crude mixture containing 3-(benzyloxypentyl)-phenol, n-pentyl ether. A solution of 6.0 gm of this crude mixture in ethanol is hydrogenated over 5% Pd on carbon for 5 hours. After filtering through celite and concentrating, pure 3-(5-hydroxypentyl)-phenol, n-pentyl ether is obtained as a clear oil by HPLC chromatography. is then stirred an additional 24 hours before being quenched with silica gel After removing the solvent the mixture is chromatographed over silica gel (1:1 hexane:ether) to yield a crude mixture After filtering through celite concentrating

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 5.0 gm of 3-Bromophenol in 60 mls of dimethylformamide is added 6.0 gm of potassium carbonate followed by 4.3 ml of 1-bromopentane. This mixture is heated to 60° C. for 6 hours and then cooled to room temperature and filtered. The filtrate is diluted with ether and washed with water and brine. After drying over magnesium sulfate and concentrating, the crude oil obtained is chromatographed over silica gel, and eluted with 3:2 hexane:ether to yield 3-bromo-phenol, n-pentyl ether as a clear oil. cooled to room temperature filtered The filtrate is diluted with ether washed with water and brine After drying over magnesium sulfate concentrating the crude oil obtained is chromatographed over silica gel eluted with 3:2 hexane

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

Procedure: At a temperature of -78° C., 19.4 ml of t-butyl lithium (1.7M) is added to 4.0 gm of the above 3-bromo-phenol, n-pentyl ether in 50 mls tetrahydrofuran; and to this is added 3.3 ml of a freshly prepared solution of Li2CuCl3 (0.10M/THF). The mixture is stirred for 10 minutes, and then 4.35 grams of the 1-bromo-5-benzyloxy pentane are added. The reaction is allowed to warm slowly to ambient temperature over 12 hours and is then stirred an additional 24 hours before being quenched with silica gel. After removing the solvent, the mixture is chromatographed over silica gel (1:1 hexane:ether) to yield a crude mixture containing 3-(benzyloxypentyl)-phenol, n-pentyl ether. A solution of 6.0 gm of this crude mixture in ethanol is hydrogenated over 5% Pd on carbon for 5 hours. After filtering through celite and concentrating, pure 3-(5-hydroxypentyl)-phenol, n-pentyl ether is obtained as a clear oil by HPLC chromatography. is then stirred an additional 24 hours before being quenched with silica gel After removing the solvent the mixture is chromatographed over silica gel (1:1 hexane:ether) to yield a crude mixture After filtering through celite concentrating

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 5.0 gm of 3-Bromophenol in 60 mls of dimethylformamide is added 6.0 gm of potassium carbonate followed by 4.3 ml of 1-bromopentane. This mixture is heated to 60° C. for 6 hours and then cooled to room temperature and filtered. The filtrate is diluted with ether and washed with water and brine. After drying over magnesium sulfate and concentrating, the crude oil obtained is chromatographed over silica gel, and eluted with 3:2 hexane:ether to yield 3-bromo-phenol, n-pentyl ether as a clear oil. cooled to room temperature filtered The filtrate is diluted with ether washed with water and brine After drying over magnesium sulfate concentrating the crude oil obtained is chromatographed over silica gel eluted with 3:2 hexane

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

Procedure: At a temperature of -78° C., 19.4 ml of t-butyl lithium (1.7M) is added to 4.0 gm of the above 3-bromo-phenol, n-pentyl ether in 50 mls tetrahydrofuran; and to this is added 3.3 ml of a freshly prepared solution of Li2CuCl3 (0.10M/THF). The mixture is stirred for 10 minutes, and then 4.35 grams of the 1-bromo-5-benzyloxy pentane are added. The reaction is allowed to warm slowly to ambient temperature over 12 hours and is then stirred an additional 24 hours before being quenched with silica gel. After removing the solvent, the mixture is chromatographed over silica gel (1:1 hexane:ether) to yield a crude mixture containing 3-(benzyloxypentyl)-phenol, n-pentyl ether. A solution of 6.0 gm of this crude mixture in ethanol is hydrogenated over 5% Pd on carbon for 5 hours. After filtering through celite and concentrating, pure 3-(5-hydroxypentyl)-phenol, n-pentyl ether is obtained as a clear oil by HPLC chromatography. is then stirred an additional 24 hours before being quenched with silica gel After removing the solvent the mixture is chromatographed over silica gel (1:1 hexane:ether) to yield a crude mixture After filtering through celite concentrating

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 5.0 gm of 3-Bromophenol in 60 mls of dimethylformamide is added 6.0 gm of potassium carbonate followed by 4.3 ml of 1-bromopentane. This mixture is heated to 60° C. for 6 hours and then cooled to room temperature and filtered. The filtrate is diluted with ether and washed with water and brine. After drying over magnesium sulfate and concentrating, the crude oil obtained is chromatographed over silica gel, and eluted with 3:2 hexane:ether to yield 3-bromo-phenol, n-pentyl ether as a clear oil. cooled to room temperature filtered The filtrate is diluted with ether washed with water and brine After drying over magnesium sulfate concentrating the crude oil obtained is chromatographed over silica gel eluted with 3:2 hexane