[4-(2-methylpropyl)phenyl]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: Lithium aluminum hydride (586 mg, 15.4 mmol) was slurried in diethyl ether (50 mL) and cooled in an ice bath. A solution of 4-isobutylbenzaldehyde (5.00 g, 30.9 mmol) in diethyl ether (30 mL) was added dropwise over 10 min and the mixture was stirred for 30 min before successive addition of water (0.6 mL), 15% aq NaOH (0.6 mL), and water (1.8 mL). The resulting precipitate was removed via filtration and the filtrate was dried (MgSO4), filtered, and evaporated in vacuo to give 4-isobutylbenzyl alcohol (4.78 g, 94%). 1H NMR (CDCl3) 7.28 (d, 2H), 7.13 (d, 2H), 4.63 (s, 2H), 2.45 (d, 2H), 1.85 (m, 1H), 0.90 (d, 6H). cooled in an ice bath The resulting precipitate was removed via filtration the filtrate was dried (MgSO4) filtered evaporated in vacuo

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

Procedure: Lithium aluminum hydride (586 mg, 15.4 mmol) was slurried in diethyl ether (50 mL) and cooled in an ice bath. A solution of 4-isobutylbenzaldehyde (5.00 g, 30.9 mmol) in diethyl ether (30 mL) was added dropwise over 10 min and the mixture was stirred for 30 min before successive addition of water (0.6 mL), 15% aq NaOH (0.6 mL), and water (1.8 mL). The resulting precipitate was removed via filtration and the filtrate was dried (MgSO4), filtered, and evaporated in vacuo to give 4-isobutylbenzyl alcohol (4.78 g, 94%). 1H NMR (CDCl3) 7.28 (d, 2H), 7.13 (d, 2H), 4.63 (s, 2H), 2.45 (d, 2H), 1.85 (m, 1H), 0.90 (d, 6H). cooled in an ice bath The resulting precipitate was removed via filtration the filtrate was dried (MgSO4) filtered evaporated in vacuo

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

Procedure: HBr gas was bubbled through a solution of (4-isobutyl-phenyl)-methanol (5 g, 28 mmol) in Et2O (50 mL) for 10–15 minutes. The reaction was stirred for 1 h and was poured onto ice (100 g). Et2O was added and the organic solution was washed with brine (2×). The organic solution was dried (MgSO4), filtered, and concentrated to provide the title compound (6 g). 1H NMR (400 MHz, CDCl3) δ 7.28 (d, 2H), 7.10 (d, 2H), 4.49 (s, 2H), 2.45 (d, 2H), 1.84 (m, 1H), 0.89 (d, 6H). was poured onto ice (100 g) the organic solution was washed with brine (2×) The organic solution was dried (MgSO4) filtered concentrated

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

Procedure: HBr gas was bubbled through a solution of (4-isobutyl-phenyl)-methanol (5 g, 28 mmol) in Et2O (50 mL) for 10–15 minutes. The reaction was stirred for 1 h and was poured onto ice (100 g). Et2O was added and the organic solution was washed with brine (2×). The organic solution was dried (MgSO4), filtered, and concentrated to provide the title compound (6 g). 1H NMR (400 MHz, CDCl3) δ 7.28 (d, 2H), 7.10 (d, 2H), 4.49 (s, 2H), 2.45 (d, 2H), 1.84 (m, 1H), 0.89 (d, 6H). was poured onto ice (100 g) the organic solution was washed with brine (2×) The organic solution was dried (MgSO4) filtered concentrated

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

Procedure: A solution of lithium aluminum hydride (30 mL, 1M in THF, 30 mmol) was added dropwise to a solution of 4-isobutylbenzoic acid (5.34 g, 30 mmol) in THF (50 mL) at 0° C. The ice bath was removed and the reaction was stirred at room temperature for 1 h. The reaction was carefully poured onto a mixture of ice and aqueous HCl (10 mL, 6N). The product was extracted into EtOAc and the organic solution was dried (MgSO4), filtered, and concentrated to obtain (4-isobutyl-phenyl)-methanol which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ 7.26 (d, 2H), 7.13 (d, 2H), 4.65 (s, 2H), 2.46 (d, 2H), 1.85 (m, 1H), 0.89 (d, 6H). The ice bath was removed The reaction was carefully poured onto a mixture of ice and aqueous HCl (10 mL, 6N) The product was extracted into EtOAc the organic solution was dried (MgSO4) filtered concentrated

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

Procedure: A solution of lithium aluminum hydride (30 mL, 1M in THF, 30 mmol) was added dropwise to a solution of 4-isobutylbenzoic acid (5.34 g, 30 mmol) in THF (50 mL) at 0° C. The ice bath was removed and the reaction was stirred at room temperature for 1 h. The reaction was carefully poured onto a mixture of ice and aqueous HCl (10 mL, 6N). The product was extracted into EtOAc and the organic solution was dried (MgSO4), filtered, and concentrated to obtain (4-isobutyl-phenyl)-methanol which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ 7.26 (d, 2H), 7.13 (d, 2H), 4.65 (s, 2H), 2.46 (d, 2H), 1.85 (m, 1H), 0.89 (d, 6H). The ice bath was removed The reaction was carefully poured onto a mixture of ice and aqueous HCl (10 mL, 6N) The product was extracted into EtOAc the organic solution was dried (MgSO4) filtered concentrated

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: HBr gas was bubbled through a solution of (4-isobutyl-phenyl)-methanol (5 g, 28 mmol) in Et2O (50 mL) for 10-15 minutes. The reaction was stirred for 1 h and was poured onto ice (100 g). Et2O was added and the organic solution was washed with brine (2×). The organic solution was dried (MgSO4), filtered, and concentrated to provide the title compound (6 g). 1H NMR (400 MHz, CDCl3) δ 7.28 (d, 2H), 7.10 (d, 2H), 4.49 (s, 2H), 2.45 (d, 2H), 1.84 (m, 1H), 0.89 (d, 6H). was poured onto ice (100 g) the organic solution was washed with brine (2×) The organic solution was dried (MgSO4) filtered concentrated

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

Procedure: HBr gas was bubbled through a solution of (4-isobutyl-phenyl)-methanol (5 g, 28 mmol) in Et2O (50 mL) for 10-15 minutes. The reaction was stirred for 1 h and was poured onto ice (100 g). Et2O was added and the organic solution was washed with brine (2×). The organic solution was dried (MgSO4), filtered, and concentrated to provide the title compound (6 g). 1H NMR (400 MHz, CDCl3) δ 7.28 (d, 2H), 7.10 (d, 2H), 4.49 (s, 2H), 2.45 (d, 2H), 1.84 (m, 1H), 0.89 (d, 6H). was poured onto ice (100 g) the organic solution was washed with brine (2×) The organic solution was dried (MgSO4) filtered concentrated