1-methoxy-2-(2-methylpropyl)benzene

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

Procedure: A solution of 1-(2-methoxyphenyl)-2-methylpropene (9a) (3.37 g, 20.8 mmol) and 10% Pd/C (300 mg) in 100 ml of anhydrous EtOH at rt was hydrogenated at 60 psi until complete conversion was determined by GC/MS (9 h). The reaction mixture was filtered through celite and concentrated in vacuo to yield 2.87 g of a clear oil (84%): 1H NMR (500 MHz, CDCl3) δ 0.90 (d, J=6.6 Hz, 6H), 1.92 (m, 1H), 2.49 (d, J=7.1 Hz, 2H), 3.82 (s, 3H), 6.88 (m, 2H), 7.10 (d, J=8.9 Hz, 1H), 7.18 (t, J=8.0 Hz, 1H); 13C NMR (125 MHz, CDCl3) δ 22.55, 28.64, 39.43, 55.22, 110.27, 120.07, 126.80, 130.22, 130.80, 157.70; HRMS (EI) Calcd for C11H16O: 164.1201. Found 164.1207. at rt was determined by GC/MS (9 h) The reaction mixture was filtered through celite and concentrated in vacuo

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

Procedure: A solution of 1-(2-methoxyphenyl)-2-methylpropene (9a) (3.37 g, 20.8 mmol) and 10% Pd/C (300 mg) in 100 ml of anhydrous EtOH at rt was hydrogenated at 60 psi until complete conversion was determined by GC/MS (9 h). The reaction mixture was filtered through celite and concentrated in vacuo to yield 2.87 g of a clear oil (84%): 1H NMR (500 MHz, CDCl3) δ 0.90 (d, J=6.6 Hz, 6H), 1.92 (m, 1H), 2.49 (d, J=7.1 Hz, 2H), 3.82 (s, 3H), 6.88 (m, 2H), 7.10 (d, J=8.9 Hz, 1H), 7.18 (t, J=8.0 Hz, 1H); 13C NMR (125 MHz, CDCl3) δ 22.55, 28.64, 39.43, 55.22, 110.27, 120.07, 126.80, 130.22, 130.80, 157.70; HRMS (EI) Calcd for C11H16O: 164.1201. Found 164.1207. at rt was determined by GC/MS (9 h) The reaction mixture was filtered through celite and concentrated in vacuo

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

Procedure: A solution of 1-(2-methoxyphenyl)-2-methylpropene (9a) (3.37 g, 20.8 mmol) and 10% Pd/C (300 mg) in 100 ml of anhydrous EtOH at rt was hydrogenated at 60 psi until complete conversion was determined by GC/MS (9 h). The reaction mixture was filtered through celite and concentrated in vacuo to yield 2.87 g of a clear oil (84%): 1H NMR (500 MHz, CDCl3) δ 0.90 (d, J=6.6 Hz, 6H), 1.92 (m, 1H), 2.49 (d, J=7.1 Hz, 2H), 3.82 (s, 3H), 6.88 (m, 2H), 7.10 (d, J=8.9 Hz, 1H), 7.18 (t, J=8.0 Hz, 1H); 13C NMR (125 MHz, CDCl3) δ 22.55, 28.64, 39.43, 55.22, 110.27, 120.07, 126.80, 130.22, 130.80, 157.70; HRMS (EI) Calcd for C11H16O: 164.1201. Found 164.1207. at rt was determined by GC/MS (9 h) The reaction mixture was filtered through celite and concentrated in vacuo

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

Procedure: A solution of 1-(2-methoxyphenyl)-2-methylpropene (9a) (3.37 g, 20.8 mmol) and 10% Pd/C (300 mg) in 100 ml of anhydrous EtOH at rt was hydrogenated at 60 psi until complete conversion was determined by GC/MS (9 h). The reaction mixture was filtered through celite and concentrated in vacuo to yield 2.87 g of a clear oil (84%): 1H NMR (500 MHz, CDCl3) δ 0.90 (d, J=6.6 Hz, 6H), 1.92 (m, 1H), 2.49 (d, J=7.1 Hz, 2H), 3.82 (s, 3H), 6.88 (m, 2H), 7.10 (d, J=8.9 Hz, 1H), 7.18 (t, J=8.0 Hz, 1H); 13C NMR (125 MHz, CDCl3) δ 22.55, 28.64, 39.43, 55.22, 110.27, 120.07, 126.80, 130.22, 130.80, 157.70; HRMS (EI) Calcd for C11H16O: 164.1201. Found 164.1207. at rt was determined by GC/MS (9 h) The reaction mixture was filtered through celite and concentrated in vacuo

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

Procedure: A solution of 1-(2-methoxyphenyl)-2-methylpropene (9a) (3.37 g, 20.8 mmol) and 10% Pd/C (300 mg) in 100 ml of anhydrous EtOH at rt was hydrogenated at 60 psi until complete conversion was determined by GC/MS (9 h). The reaction mixture was filtered through celite and concentrated in vacuo to yield 2.87 g of a clear oil (84%): 1H NMR (500 MHz, CDCl3) δ 0.90 (d, J=6.6 Hz, 6H), 1.92 (m, 1H), 2.49 (d, J=7.1 Hz, 2H), 3.82 (s, 3H), 6.88 (m, 2H), 7.10 (d, J=8.9 Hz, 1H), 7.18 (t, J=8.0 Hz, 1H); 13C NMR (125 MHz, CDCl3) δ 22.55, 28.64, 39.43, 55.22, 110.27, 120.07, 126.80, 130.22, 130.80, 157.70; HRMS (EI) Calcd for C11H16O: 164.1201. Found 164.1207. at rt was determined by GC/MS (9 h) The reaction mixture was filtered through celite and concentrated in vacuo

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

Procedure: A solution of 1-(2-methoxyphenyl)-2-methylpropene (9a) (3.37 g, 20.8 mmol) and 10% Pd/C (300 mg) in 100 ml of anhydrous EtOH at rt was hydrogenated at 60 psi until complete conversion was determined by GC/MS (9 h). The reaction mixture was filtered through celite and concentrated in vacuo to yield 2.87 g of a clear oil (84%): 1H NMR (500 MHz, CDCl3) δ 0.90 (d, J=6.6 Hz, 6H), 1.92 (m, 1H), 2.49 (d, J=7.1 Hz, 2H), 3.82 (s, 3H), 6.88 (m, 2H), 7.10 (d, J=8.9 Hz, 1H), 7.18 (t, J=8.0 Hz, 1H); 13C NMR (125 MHz, CDCl3) δ 22.55, 28.64, 39.43, 55.22, 110.27, 120.07, 126.80, 130.22, 130.80, 157.70; HRMS (EI) Calcd for C11H16O: 164.1201. Found 164.1207. at rt was determined by GC/MS (9 h) The reaction mixture was filtered through celite and concentrated in vacuo