ethyl 4-(4-hydroxyphenoxy)butanoate

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

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

Procedure: A solution of 5.07 g of ethyl 4-(4-hydroxyphenoxy)butyrate in 23 ml of ether is added dropwise to a mixture of 1.72 g of lithium aluminum hydride in 90 ml of ether at a rate which maintains a gentle reflux. The mixture is stirred at ambient temperature for 6 hours, and then water is carefully added followed by 3N HCl to dissolve all solids. After separating the ether phase and extracting the aqueous phase twice with ether, the combined ether phases are washed with saturated NaHCO3, water, and brine and dried over MgSO4. Filtration and concentration yields 4-(4-hydroxyphenoxy) butan-1-ol as a white solid. to dissolve all solids After separating the ether phase extracting the aqueous phase twice with ether the combined ether phases are washed with saturated NaHCO3, water, and brine dried over MgSO4 Filtration and concentration

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

Procedure: A solution of 5.07 g of ethyl 4-(4-hydroxyphenoxy)butyrate in 23 ml of ether is added dropwise to a mixture of 1.72 g of lithium aluminum hydride in 90 ml of ether at a rate which maintains a gentle reflux. The mixture is stirred at ambient temperature for 6 hours, and then water is carefully added followed by 3N HCl to dissolve all solids. After separating the ether phase and extracting the aqueous phase twice with ether, the combined ether phases are washed with saturated NaHCO3, water, and brine and dried over MgSO4. Filtration and concentration yields 4-(4-hydroxyphenoxy) butan-1-ol as a white solid. to dissolve all solids After separating the ether phase extracting the aqueous phase twice with ether the combined ether phases are washed with saturated NaHCO3, water, and brine dried over MgSO4 Filtration and concentration

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

Procedure: A solution of 5.07 g of ethyl 4-(4-hydroxyphenoxy)butyrate in 23 ml of ether is added dropwise to a mixture of 1.72 g of lithium aluminum hydride in 90 ml of ether at a rate which maintains a gentle reflux. The mixture is stirred at ambient temperature for 6 hours, and then water is carefully added followed by 3N HCl to dissolve all solids. After separating the ether phase and extracting the aqueous phase twice with ether, the combined ether phases are washed with saturated NaHCO3, water, and brine and dried over MgSO4. Filtration and concentration yields 4-(4-hydroxyphenoxy)butan-1-ol as a white solid. to dissolve all solids After separating the ether phase extracting the aqueous phase twice with ether the combined ether phases are washed with saturated NaHCO3, water, and brine dried over MgSO4 Filtration and concentration

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

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

Procedure: A solution of 5.07 g of ethyl 4-(4-hydroxyphenoxy)butyrate in 23 ml of ether is added dropwise to a mixture of 1.72 g of lithium aluminum hydride in 90 ml of ether at a rate which maintains a gentle reflux. The mixture is stirred at ambient temperature for 6 hours, and then water is carefully added followed by 3N HCl to dissolve all solids. After separating the ether phase and extracting the aqueous phase twice with ether, the combined ether phases are washed with saturated NaHCO3, water, and brine and dried over MgSO4. Filtration and concentration yields 4-(4-hydroxyphenoxy)butan-1-ol as a white solid. to dissolve all solids After separating the ether phase extracting the aqueous phase twice with ether the combined ether phases are washed with saturated NaHCO3, water, and brine dried over MgSO4 Filtration and concentration

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

Procedure: To a solution of 3.58 g (0.011 mol) of 4-(4-Benzyloxy-phenoxy)-butyric acid ethyl ester in 200 mL of ethanol was added 0.81 g of 5% palladium on carbon and the resulting mixture was shaken under 35 psi of hydrogen for 4 h. The resulting mixture was filtered through Magnesol® and concentrated in vacuo to provide 1.97 g of the phenol as a grey solid. Electrospray Mass Spec: 225 (M+H)+ The resulting mixture was filtered through Magnesol® concentrated in vacuo

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

Procedure: To a solution of 3.58 g (0.011 mol) of 4-(4-Benzyloxy-phenoxy)-butyric acid ethyl ester in 200 mL of ethanol was added 0.81 g of 5% palladium on carbon and the resulting mixture was shaken under 35 psi of hydrogen for 4 h. The resulting mixture was filtered through Magnesol® and concentrated in vacuo to provide 1.97 g of the phenol as a grey solid. Electrospray Mass Spec: 225 (M+H)+ The resulting mixture was filtered through Magnesol® concentrated in vacuo

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

Procedure: To a solution of 4-hydroxyphenol (3.3 g, 30 mmol) in ethanol (60 mL) was added K2CO3 (6.21 g, 45 mmol), Bu4NI (1.11 g, 3 mmol), and ethyl 4-bromobutanoate (4.68 g, 24 mmol). The resulting mixture was stirred at 60° C. overnight and filtered. To the filtrate was added water, and extracted with ethyl acetate, washed with brine, dried over Na2SO4 and concentrated. The residue was purified by column chromatograph on silica gel (ethyl acetate in petroleum ether, 10% v/v) to afford title product 0112-54 (1.6 g, 30%) as a brown solid. LCMS: 247 [M+23]+. 1H NMR (400 MHz, DMSO-d6): δ 1.26 (t, J=7.2 Hz, 3H), 2.08 (m, 2H), 2.51 (t, J=7.2 Hz, 2H), 3.93 (t, J=6.0 Hz, 2H), 4.15 (q, J=7.2 Hz, 2H), 6.75 (s, 4H). filtered To the filtrate was added water extracted with ethyl acetate washed with brine dried over Na2SO4 concentrated The residue was purified by column chromatograph on silica gel (ethyl acetate in petroleum ether, 10% v/v)

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

Procedure: To a solution of 4-hydroxyphenol (3.3 g, 30 mmol) in ethanol (60 mL) was added K2CO3 (6.21 g, 45 mmol), Bu4NI (1.11 g, 3 mmol), and ethyl 4-bromobutanoate (4.68 g, 24 mmol). The resulting mixture was stirred at 60° C. overnight and filtered. To the filtrate was added water, and extracted with ethyl acetate, washed with brine, dried over Na2SO4 and concentrated. The residue was purified by column chromatograph on silica gel (ethyl acetate in petroleum ether, 10% v/v) to afford title product 0112-54 (1.6 g, 30%) as a brown solid. LCMS: 247 [M+23]+. 1H NMR (400 MHz, DMSO-d6): δ 1.26 (t, J=7.2 Hz, 3H), 2.08 (m, 2H), 2.51 (t, J=7.2 Hz, 2H), 3.93 (t, J=6.0 Hz, 2H), 4.15 (q, J=7.2 Hz, 2H), 6.75 (s, 4H). filtered To the filtrate was added water extracted with ethyl acetate washed with brine dried over Na2SO4 concentrated The residue was purified by column chromatograph on silica gel (ethyl acetate in petroleum ether, 10% v/v)

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

Procedure: A solution of 5.07 g of ethyl 4-(4-hydroxyphenoxy)butyrate in 23 ml of ether is added dropwise to a mixture of 1.72 g of lithium aluminum hydride in 90 ml of ether at a rate which maintains a gentle reflux. The mixture is stirred at ambient temperature for 6 hours, and then water is carefully added followed by 3N HCl to dissolve all solids. After separating the ether phase and extracting the aqueous phase twice with ether, the combined ether phases are washed with saturated NaHCO3, water, and brine and dried over MgSO4. Filtration and concentration yields 4-(4-hydroxyphenoxy) butan-1-ol as a white solid. to dissolve all solids After separating the ether phase extracting the aqueous phase twice with ether the combined ether phases are washed with saturated NaHCO3, water, and brine dried over MgSO4 Filtration and concentration

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