(2-butoxyphenyl)methanol

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: 12.4 g (90.5 mmol) of butyl bromide, 11.2 g (90.5 mmol) of 2-hydroxybenzyl alcohol and 12.5 g (90.5 mmol) of potassium carbonate in 270 ml of 2-propanol are heated at reflux overnight. The suspension is cooled, taken up in ethyl acetate and washed with 1N aqueous sodium hydroxide solution and water, dried over magnesium sulfate and concentrated under reduced pressure. at reflux overnight The suspension is cooled washed with 1N aqueous sodium hydroxide solution and water dried over magnesium sulfate concentrated under reduced pressure

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

Procedure: 12.4 g (90.5 mmol) of butyl bromide, 11.2 g (90.5 mmol) of 2-hydroxybenzyl alcohol and 12.5 g (90.5 mmol) of potassium carbonate in 270 ml of 2-propanol are heated at reflux overnight. The suspension is cooled, taken up in ethyl acetate and washed with 1N aqueous sodium hydroxide solution and water, dried over magnesium sulfate and concentrated under reduced pressure. at reflux overnight The suspension is cooled washed with 1N aqueous sodium hydroxide solution and water dried over magnesium sulfate concentrated under reduced pressure

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

Procedure: 12.4 g (90.5 mmol) of butyl bromide, 11.2 g (90.5 mmol) of 2-hydroxybenzyl alcohol and 12.5 g (90.5 mmol) of potassium carbonate in 270 ml of 2-propanol are heated at reflux overnight. The suspension is cooled, taken up in ethyl acetate and washed with 1N aqueous sodium hydroxide solution and water, dried over magnesium sulfate and concentrated under reduced pressure. at reflux overnight The suspension is cooled washed with 1N aqueous sodium hydroxide solution and water dried over magnesium sulfate concentrated under reduced pressure

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

Procedure: A solution of 2-(hydroxymethyl)phenol (1.24 g, 10 mmol, Aldrich) and 1-bromobutane (1.18 ml, 11 mmol, Acros) in ethanol (5 ml) (total volume approximately 7 ml) was mixed in a flow reactor (Vapourtec R4, 30 ml PFA tubing, 110° C.) with a solution of aqueous NaOH (2N, 5 ml, 10 mmol) in water (2 ml). The reagents were each pumped at 0.5 ml/min), giving a reaction time of 30 minutes. After the 30 ml reactor, the solution passed through a second “cooling” reactor (5 ml) at 50° C. At the reactor output, a 250 psi back pressure regulator was used. After all starting solutions had been consumed, the system was purged with an additional 70 ml solvents (1:1, ethanol:water). The collected material was concentrated in vacuo. The residue was partitioned between water and EtOAc, and treated with saturated aqueous sodium bicarbonate solution. The aqueous phase was further extracted with EtOAc, and the combined organic extracts were dried (hydrophobic frit) and concentrated in vacuo. The residue was purified on silica (100 g) using 0-100% ethyl acetate-cyclohexane. The appropriate fractions were combined and concentrated in vacuo to give the title compound (1.4 g); LCMS: (System 4) tRET=2.51 min, no MH+ detected. giving a reaction time of 30 minutes After all starting solutions had been consumed the system was purged with an additional 70 ml solvents (1:1, ethanol:water) The collected material was concentrated in vacuo The residue was partitioned between water and EtOAc treated with saturated aqueous sodium bicarbonate solution The aqueous phase was further extracted with EtOAc the combined organic extracts were dried (hydrophobic frit) concentrated in vacuo The residue was purified on silica (100 g) concentrated in vacuo

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

Procedure: 2-Hydroxymethyl phenol (1.2 g, 9.6 mmol) was dissolved in 10 mL of dry acetonitrile. Potassium carbonate (1.3 g, 9.6 mmol) and 1-iodobutane (1 mL, 8.8 mmol) were added and the reaction was stirred at room temperature for 3 days and at 50° C. for 1 day. The solvent was removed and the residue partitioned between ethyl acetate and 1N hydrochloric acid. The acidic aqueous layer was extracted with ethyl acetate(3×25 mL). The combined organic extracts were washed with 0.5 N sodium hydroxide (3×20 mL), dried over MgSO4, filtered and concentrated to provide the title compound (800 mg, 50% yield) as a colorless oil. The solvent was removed the residue partitioned between ethyl acetate and 1N hydrochloric acid The acidic aqueous layer was extracted with ethyl acetate(3×25 mL) The combined organic extracts were washed with 0.5 N sodium hydroxide (3×20 mL) dried over MgSO4 filtered concentrated

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

Procedure: A solution of 2-(hydroxymethyl)phenol (Aldrich; 1.24 g, 10 mmol) and 1-bromobutane (Acros; 1.18 ml, 11 mmol) in ethanol (5 ml) (total volume approximately 7 ml) was mixed in a flow reactor (Vapourtec R4, 30 ml PFA tubing, 110° C.) with a solution of aqueous NaOH (2 N, 5 ml, 10 mmol) in water (2 ml). The reagents were each pumped at 0.5 ml/min), giving a reaction time of 30 minutes. After the 30 ml reactor, the solution passed through a second “cooling” reactor (5 ml) at 50° C. At the reactor output, a 250 psi back pressure regulator was used. After all starting solutions had been consumed, the system was purged with an additional 70 ml solvent (1:1, ethanol:water). The collected material was concentrated in vacuo. The residue was partitioned between water and EtOAc, and treated with saturated aqueous sodium bicarbonate solution. The aqueous phase was further extracted with EtOAc, and the combined organic extracts were dried (hydrophobic frit) and concentrated in vacuo. The residue was purified on silica (100 g) using 0-100% ethyl acetate-cyclohexane. The appropriate fractions were combined and concentrated in vacuo to give the title compound (1.4 g); LCMS (System 4): MNH4+=198, tRET=2.51 min. giving a reaction time of 30 minutes After all starting solutions had been consumed the system was purged with an additional 70 ml solvent (1:1, ethanol:water) The collected material was concentrated in vacuo The residue was partitioned between water and EtOAc treated with saturated aqueous sodium bicarbonate solution The aqueous phase was further extracted with EtOAc the combined organic extracts were dried (hydrophobic frit) concentrated in vacuo The residue was purified on silica (100 g) concentrated in vacuo