[3-[(2-methylpropan-2-yl)oxy]phenyl]methanol

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

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

Procedure: To a solution of (3-tert-butoxy-phenyl) methanol (4.02 g, 0.022 mol) and tetrabutylammonium hydrogen sulfate (0.379 g, 0.00115 mol) in 50% NaOH solution (6 mL) and benzene (15 mL) Was added 1,4-dibromobutane (7.99 mL, 0.067 mol) with vigorous stirring at ambient temperature. After stirring for 8 h, the mixture was partitioned between H2O and EtOAc. The organic layer was separated, washed with brine, dried (MgSO4), filtered, and concentrated to give the title compound after purification on an ISCO Combiflash eluting with 0-10% EtOAc/hexane. After stirring for 8 h the mixture was partitioned between H2O and EtOAc The organic layer was separated washed with brine dried (MgSO4) filtered concentrated

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

Procedure: To a suspension of LiAlH4 (1.707 g, 0.045 mol) in anhydrous diethyl ether (80 mL) in a 3-necked rb flask equipped with addition funnel at 0° C. in an ice-water bath was added dropwise a solution of 3-tert-butoxy-benzoic acid ethyl ester (5.0 g, 0.0225 mol) in ether (20 mL). The reaction mixture was left to warm to rt over 15 min, then cooled in an ice-water bath and quenched by dropwise addition of H2O. The mixture was partitioned between ether and H2O, the aqueous layer washed with ether (2×30 mL), the organics combined, washed with brine, dried (MgSO4), filtered and concentrated to give 3.70 g (82%) of the title compound. equipped with addition funnel at 0° C. in an ice-water bath The reaction mixture was left cooled in an ice-water bath quenched by dropwise addition of H2O The mixture was partitioned between ether and H2O the aqueous layer washed with ether (2×30 mL) washed with brine dried (MgSO4) filtered concentrated

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

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

Procedure: To a solution of (3-tert-butoxy-phenyl) methanol (4.02 g, 0.022 mol) and tetrabutylammonium hydrogen sulfate (0.379 g, 0.00115 mol) in 50% NaOH solution (6 mL) and benzene (15 mL) Was added 1,4-dibromobutane (7.99 mL, 0.067 mol) with vigorous stirring at ambient temperature. After stirring for 8 h, the mixture was partitioned between H2O and EtOAc. The organic layer was separated, washed with brine, dried (MgSO4), filtered, and concentrated to give the title compound after purification on an ISCO Combiflash eluting with 0-10% EtOAc/hexane. After stirring for 8 h the mixture was partitioned between H2O and EtOAc The organic layer was separated washed with brine dried (MgSO4) filtered concentrated

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

Procedure: To a solution of (3-tert-butoxy-phenyl) methanol (4.02 g, 0.022 mol) and tetrabutylammonium hydrogen sulfate (0.379 g, 0.00115 mol) in 50% NaOH solution (6 mL) and benzene (15 mL) Was added 1,4-dibromobutane (7.99 mL, 0.067 mol) with vigorous stirring at ambient temperature. After stirring for 8 h, the mixture was partitioned between H2O and EtOAc. The organic layer was separated, washed with brine, dried (MgSO4), filtered, and concentrated to give the title compound after purification on an ISCO Combiflash eluting with 0-10% EtOAc/hexane. After stirring for 8 h the mixture was partitioned between H2O and EtOAc The organic layer was separated washed with brine dried (MgSO4) filtered concentrated

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

Procedure: To a suspension of LiAlH4 (1.707 g, 0.045 mol) in anhydrous diethyl ether (80 mL) in a 3-necked rb flask equipped with addition funnel at 0° C. in an ice-water bath was added dropwise a solution of 3-tert-butoxy-benzoic acid ethyl ester (5.0 g, 0.0225 mol) in ether (20 mL). The reaction mixture was left to warm to rt over 15 min, then cooled in an ice-water bath and quenched by dropwise addition of H2O. The mixture was partitioned between ether and H2O, the aqueous layer washed with ether (2×30 mL), the organics combined, washed with brine, dried (MgSO4), filtered and concentrated to give 3.70 g (82%) of the title compound. equipped with addition funnel at 0° C. in an ice-water bath The reaction mixture was left cooled in an ice-water bath quenched by dropwise addition of H2O The mixture was partitioned between ether and H2O the aqueous layer washed with ether (2×30 mL) washed with brine dried (MgSO4) filtered concentrated

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

Procedure: To a solution of ethyl 3-tert-butyloxybenzoate (16.7 g, 80 mmol) in tetrahydrofuran (100 ml) was added lithium aluminum hydride (4.55 g, 120 mmol) by small portions under ice-cooling. The mixture was stirred at room temperature for 1 hr. and water (10 ml) was added under ice-cooling to allow decomposition. Insoluble material was filtered off and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=3:1-2:1) to give the objective substance (12.8 g, 88%) as an oil. cooling cooling Insoluble material was filtered off the solvent was evaporated under reduced pressure The residue was purified by silica gel chromatography (hexane:ethyl acetate=3:1-2:1) to give the objective substance (12.8 g, 88%) as an oil

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

Procedure: To a solution of (3-tert-butoxy-phenyl) methanol (4.02 g, 0.022 mol) and tetrabutylammonium hydrogen sulfate (0.379 g, 0.00115 mol) in 50% NaOH solution (6 mL) and benzene (15 mL) Was added 1,4-dibromobutane (7.99 mL, 0.067 mol) with vigorous stirring at ambient temperature. After stirring for 8 h, the mixture was partitioned between H2O and EtOAc. The organic layer was separated, washed with brine, dried (MgSO4), filtered, and concentrated to give the title compound after purification on an ISCO Combiflash eluting with 0-10% EtOAc/hexane. After stirring for 8 h the mixture was partitioned between H2O and EtOAc The organic layer was separated washed with brine dried (MgSO4) filtered concentrated

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

Procedure: To a suspension of LiAlH4 (1.707 g, 0.045 mol) in anhydrous diethyl ether (80 mL) in a 3-necked rb flask equipped with addition funnel at 0° C. in an ice-water bath was added dropwise a solution of 3-tert-butoxy-benzoic acid ethyl ester (5.0 g, 0.0225 mol) in ether (20 mL). The reaction mixture was left to warm to rt over 15 min, then cooled in an ice-water bath and quenched by dropwise addition of H2O. The mixture was partitioned between ether and H2O, the aqueous layer washed with ether (2×30 mL), the organics combined, washed with brine, dried (MgSO4), filtered and concentrated to give 3.70 g (82%) of the title compound. equipped with addition funnel at 0° C. in an ice-water bath The reaction mixture was left cooled in an ice-water bath quenched by dropwise addition of H2O The mixture was partitioned between ether and H2O the aqueous layer washed with ether (2×30 mL) washed with brine dried (MgSO4) filtered concentrated