3-pentoxyphenol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Prepared according to the method described in Example E above from 3-(n-pentoxy)phenol (18.0 g; 0.1 mol; from Example C above) and 1,2-dibromoethane (100 ml; 1.16 mol). Following work up the residue was chromatographed on silica gel with diisopropyl ether as eluent to yield 26.1 g (91%) of the tide compound as an oil which subsequently crystallised (96% purity). MW=287 (GCMS) Prepared was chromatographed on silica gel with diisopropyl ether as eluent

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

Procedure: Prepared according to the method described in Example A above from resorcinol (55 g; 0.5 mol) and n-pentylbromide (83.1 g; 0.55 mol) to yield 36.0 g (40%) of the title compound as an oil (92% purity). bp 128-131° C. (5 mm Hg) MW=180 (GC-MS) Prepared

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

Procedure: A mixture of 7.3 g of 60% NaH in 190 ml of anhydrous dimethylformamide is cooled in an ice bath. To this mixture is added 22.0 g of 3-pentyloxyphenol dissolved in 50 ml of anhydrous dimethylformamide. This mixture is then stirred at room temperature for 45 minutes; 23.2 ml of ethyl 4-bromobutyrate are added; and the resultant mixture is stirred at 60° C. for 17 hours. The solvent is removed under vacuum and the residue worked up as above. The residue is flash chromatographed on normal phase silica gel using a gradient from hexane to a 4:1 ratio of hexane:ether to yield ethyl 4-(3-pentyloxyphenoxy)butyrate as a clear oil. is cooled in an ice bath The solvent is removed under vacuum chromatographed on normal phase silica gel using a gradient from hexane to a 4:1 ratio of hexane

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

Procedure: A mixture of 0.80 g of 60% NaH in 28 ml of anhydrous dimethylformamide is cooled in an ice bath. To this is added 3.01 g of the above 3-pentyloxyphenol oil dissolved in 7 ml of anhydrous dimethylformamide. This mixture is then stirred at room temperature for 45 minutes; 1.81 ml of 3-Bromopropanol are added; and the resultant mixture is stirred at 60° C. for 17 hours. The solvent is removed under vacuum, and the residue worked up in same manner as above. The residue obtained is flash chromatographed on normal phase silica gel eluting with a 3:2 ratio of hexane:ether to yield 3-[3-(pentyloxy)phenoxy]propanol as a pale yellow oil. is cooled in an ice bath The solvent is removed under vacuum The residue obtained chromatographed on normal phase silica gel eluting with a 3:2 ratio of hexane

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

Procedure: A mixture of 24.8 ml of 1-Bromopentane, 66.0 g of resorcinol, and 41.5 g of potassium carbonate is stirred in 400 ml of anhydrous dimethylformamide at 60° C. for 17 hours. This mixture is filtered through Celite and concentrated under vacuum. The residue is taken up in water and extracted 3 times with ether. The combined extracts are washed with saturated sodium chloride, dried over magnesium sulfate, filtered, and concentrated under vacuum. The residue is flash chromatographed on normal phase silica gel eluting with a 4:1 ratio of hexane:ether to yield 3-pentyloxyphenol as a clear oil. This mixture is filtered through Celite concentrated under vacuum extracted 3 times with ether The combined extracts are washed with saturated sodium chloride dried over magnesium sulfate filtered concentrated under vacuum chromatographed on normal phase silica gel eluting with a 4:1 ratio of hexane

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

Procedure: A mixture of 24.8 ml of 1-Bromopentane, 66.0 g of resorcinol, and 41.5 g of potassium carbonate is stirred in 400 ml of anhydrous dimethylformamide at 60° C. for 17 hours. This mixture is filtered through Celite and concentrated under vacuum. The residue is taken up in water and extracted 3 times with ether. The combined extracts are washed with saturated sodium chloride, dried over magnesium sulfate, filtered, and concentrated under vacuum. The residue is flash chromatographed on normal phase silica gel eluting with a 4:1 ratio of hexane:ether to yield 3-pentyloxyphenol as a clear oil. This mixture is filtered through Celite concentrated under vacuum extracted 3 times with ether The combined extracts are washed with saturated sodium chloride dried over magnesium sulfate filtered concentrated under vacuum chromatographed on normal phase silica gel eluting with a 4:1 ratio of hexane

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

Procedure: Prepared according to the method described in Example E above from 3-(n-pentoxy)phenol (18.0 g; 0.1 mol; from Example C above) and 1,2-dibromoethane (100 ml; 1.16 mol). Following work up the residue was chromatographed on silica gel with diisopropyl ether as eluent to yield 26.1 g (91%) of the tide compound as an oil which subsequently crystallised (96% purity). MW=287 (GCMS) Prepared was chromatographed on silica gel with diisopropyl ether as eluent

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

Procedure: Prepared according to the method described in Example E above from 3-(n-pentoxy)phenol (18.0 g; 0.1 mol; from Example C above) and 1,2-dibromoethane (100 ml; 1.16 mol). Following work up the residue was chromatographed on silica gel with diisopropyl ether as eluent to yield 26.1 g (91%) of the tide compound as an oil which subsequently crystallised (96% purity). MW=287 (GCMS) Prepared was chromatographed on silica gel with diisopropyl ether as eluent

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

Procedure: Prepared according to the method described in Example A above from resorcinol (55 g; 0.5 mol) and n-pentylbromide (83.1 g; 0.55 mol) to yield 36.0 g (40%) of the title compound as an oil (92% purity). bp 128-131° C. (5 mm Hg) MW=180 (GC-MS) Prepared

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

Procedure: Prepared according to the method described in Example A above from resorcinol (55 g; 0.5 mol) and n-pentylbromide (83.1 g; 0.55 mol) to yield 36.0 g (40%) of the title compound as an oil (92% purity). bp 128-131° C. (5 mm Hg) MW=180 (GC-MS) Prepared