(4-octylphenyl)methanol

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

Procedure: PBr3 (0.23 ml) was added drop wise to a stirred solution of the product of Step A (0.082 g; 0.37 mmol) in Et2O (2 ml) at −15° C. The mixture was allowed to warm up to room temperature and the stirring was continued for 4 h. This was poured onto ice (5 g) and the product was extracted with fresh Et2O (2×10 ml). The combined extracts were washed with 5% NaHCO3, H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by FCC (SiO2, hexane) to give the title compound (0.04 g; 40%) as a colourless solid. 1H-NMR (CDCl3) 7.28 (d, 2H, J=8 Hz); 7.13 (d, 2H, J=8 Hz); 4.48 (s, 2H); 2.57 (t, 2H, J=7.9 Hz); 1.57 (m, 2H); 1.26 (m, 10H); 0.86 (t, 3H, J=7 Hz). This was poured onto ice (5 g) the product was extracted with fresh Et2O (2×10 ml) The combined extracts were washed with 5% NaHCO3, H2O, brine dried over anhydrous MgSO4 filtered The filtrate was evaporated under reduced pressure the residue was purified by FCC (SiO2, hexane)

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

Procedure: PBr3 (0.23 ml) was added drop wise to a stirred solution of the product of Step A (0.082 g; 0.37 mmol) in Et2O (2 ml) at −15° C. The mixture was allowed to warm up to room temperature and the stirring was continued for 4 h. This was poured onto ice (5 g) and the product was extracted with fresh Et2O (2×10 ml). The combined extracts were washed with 5% NaHCO3, H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by FCC (SiO2, hexane) to give the title compound (0.04 g; 40%) as a colourless solid. 1H-NMR (CDCl3) 7.28 (d, 2H, J=8 Hz); 7.13 (d, 2H, J=8 Hz); 4.48 (s, 2H); 2.57 (t, 2H, J=7.9 Hz); 1.57 (m, 2H); 1.26 (m, 10H); 0.86 (t, 3H, J=7 Hz). This was poured onto ice (5 g) the product was extracted with fresh Et2O (2×10 ml) The combined extracts were washed with 5% NaHCO3, H2O, brine dried over anhydrous MgSO4 filtered The filtrate was evaporated under reduced pressure the residue was purified by FCC (SiO2, hexane)

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

Procedure: PBr3 (0.23 ml) was added drop wise to a stirred solution of the product of Step B (0.082 g; 0.37 mmol) in Et2O (2 ml) at −15° C. The mixture was allowed to warm up to room temperature and the stirring was continued for 4 h. This was poured onto ice (5 g) and the product was extracted with fresh Et2O (2×10 ml). The combined extracts were washed with 5% NaHCO3, H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by FCC (SiO2, hexane) to give the title compound (0.04 g; 40%) as a colourless solid. 1H-NMR (CDCl3) 0.86 (tr, 3H, J=7 Hz); 1.26 (m, 10H); 1.57 (m, 2H); 2.57 (tr, 2H, J=7.9 Hz); 4.48 (s, 2H); 7.13 (d, 2H, J=8 Hz); 7.28 (d, 2H, J=8 Hz). This was poured onto ice (5 g) the product was extracted with fresh Et2O (2×10 ml) The combined extracts were washed with 5% NaHCO3, H2O, brine dried over anhydrous MgSO4 filtered The filtrate was evaporated under reduced pressure the residue was purified by FCC (SiO2, hexane)

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

Procedure: A mixture of 16.2 g (68 mMols) of 4-octylbenzyl chloride, 41,8 g (0.43 mols) of potassium acetate and 200 ml of glacial acetic acid was heated for 20 h to 130° C. After cooling, the mixture was poured into approximately 1 liter of water and the aqueous phase was extracted with tert.-butyl methyl ether. The organic phase was washed twice with water, repeatedly with potassium hydrogen carbonate solution (2N) and then with saturated sodium chloride solution. After the solvent had been distilled off, the residue was taken up in 160 ml of 1,2-dimethoxyethane and, after the addition of 64 g of sodium hydroxide in 130 ml of water, the solution was heated for 45 h to boiling point. After the solvent had been distilled off, the residue was extracted with tert.-butyl methyl ether, the ether phase was washed with water, the solvent was distilled off, the residue was taken up in petroleum ether and the solution was reconcentrated by evaporation after treatment with active carbon and fuller's earth. Fractionation under reduced pressure produced 8 g (54% of theoretical) of 4-octylbenzyl alcohol boiling at 128° C./0.11 mbar and having a refractive index n of 1.5033. was heated for 20 h to 130° C After cooling the aqueous phase was extracted with tert.-butyl methyl ether The organic phase was washed twice with water, repeatedly with potassium hydrogen carbonate solution (2N) After the solvent had been distilled off after the addition of 64 g of sodium hydroxide in 130 ml of water the solution was heated for 45 h After the solvent had been distilled off the residue was extracted with tert.-butyl methyl ether the ether phase was washed with water the solvent was distilled off the solution was reconcentrated by evaporation after treatment with active carbon and fuller's earth

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

Procedure: A mixture of 16.2 g (68 mMols) of 4-octylbenzyl chloride, 41,8 g (0.43 mols) of potassium acetate and 200 ml of glacial acetic acid was heated for 20 h to 130° C. After cooling, the mixture was poured into approximately 1 liter of water and the aqueous phase was extracted with tert.-butyl methyl ether. The organic phase was washed twice with water, repeatedly with potassium hydrogen carbonate solution (2N) and then with saturated sodium chloride solution. After the solvent had been distilled off, the residue was taken up in 160 ml of 1,2-dimethoxyethane and, after the addition of 64 g of sodium hydroxide in 130 ml of water, the solution was heated for 45 h to boiling point. After the solvent had been distilled off, the residue was extracted with tert.-butyl methyl ether, the ether phase was washed with water, the solvent was distilled off, the residue was taken up in petroleum ether and the solution was reconcentrated by evaporation after treatment with active carbon and fuller's earth. Fractionation under reduced pressure produced 8 g (54% of theoretical) of 4-octylbenzyl alcohol boiling at 128° C./0.11 mbar and having a refractive index n of 1.5033. was heated for 20 h to 130° C After cooling the aqueous phase was extracted with tert.-butyl methyl ether The organic phase was washed twice with water, repeatedly with potassium hydrogen carbonate solution (2N) After the solvent had been distilled off after the addition of 64 g of sodium hydroxide in 130 ml of water the solution was heated for 45 h After the solvent had been distilled off the residue was extracted with tert.-butyl methyl ether the ether phase was washed with water the solvent was distilled off the solution was reconcentrated by evaporation after treatment with active carbon and fuller's earth

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

Procedure: PBr3 (0.23 ml) was added drop wise to a stirred solution of the product of Step A (0.082 g; 0.37 mmol) in Et2O (2 ml) at −15° C. The mixture was allowed to warm up to room temperature and the stirring was continued for 4 h. This was poured onto ice (5 g) and the product was extracted with fresh Et2O (2×10 ml). The combined extracts were washed with 5% NaHCO3, H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by FCC (SiO2, hexane) to give the title compound (0.04 g; 40%) as a colourless solid. 1H-NMR (CDCl3) 7.28 (d, 2H, J=8 Hz); 7.13 (d, 2H, J=8 Hz); 4.48 (s, 2H); 2.57 (t, 2H, J=7.9 Hz); 1.57 (m, 2H); 1.26 (m, 10H); 0.86 (t, 3H, J=7 Hz). This was poured onto ice (5 g) the product was extracted with fresh Et2O (2×10 ml) The combined extracts were washed with 5% NaHCO3, H2O, brine dried over anhydrous MgSO4 filtered The filtrate was evaporated under reduced pressure the residue was purified by FCC (SiO2, hexane)

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

Procedure: PBr3 (0.23 ml) was added drop wise to a stirred solution of the product of Step A (0.082 g; 0.37 mmol) in Et2O (2 ml) at −15° C. The mixture was allowed to warm up to room temperature and the stirring was continued for 4 h. This was poured onto ice (5 g) and the product was extracted with fresh Et2O (2×10 ml). The combined extracts were washed with 5% NaHCO3, H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by FCC (SiO2, hexane) to give the title compound (0.04 g; 40%) as a colourless solid. 1H-NMR (CDCl3) 7.28 (d, 2H, J=8 Hz); 7.13 (d, 2H, J=8 Hz); 4.48 (s, 2H); 2.57 (t, 2H, J=7.9 Hz); 1.57 (m, 2H); 1.26 (m, 10H); 0.86 (t, 3H, J=7 Hz). This was poured onto ice (5 g) the product was extracted with fresh Et2O (2×10 ml) The combined extracts were washed with 5% NaHCO3, H2O, brine dried over anhydrous MgSO4 filtered The filtrate was evaporated under reduced pressure the residue was purified by FCC (SiO2, hexane)

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

Procedure: PBr3 (0.23 ml) was added drop wise to a stirred solution of the product of Step B (0.082 g; 0.37 mmol) in Et2O (2 ml) at −15° C. The mixture was allowed to warm up to room temperature and the stirring was continued for 4 h. This was poured onto ice (5 g) and the product was extracted with fresh Et2O (2×10 ml). The combined extracts were washed with 5% NaHCO3, H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by FCC (SiO2, hexane) to give the title compound (0.04 g; 40%) as a colourless solid. 1H-NMR (CDCl3) 0.86 (tr, 3H, J=7 Hz); 1.26 (m, 10H); 1.57 (m, 2H); 2.57 (tr, 2H, J=7.9 Hz); 4.48 (s, 2H); 7.13 (d, 2H, J=8 Hz); 7.28 (d, 2H, J=8 Hz). This was poured onto ice (5 g) the product was extracted with fresh Et2O (2×10 ml) The combined extracts were washed with 5% NaHCO3, H2O, brine dried over anhydrous MgSO4 filtered The filtrate was evaporated under reduced pressure the residue was purified by FCC (SiO2, hexane)

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

Procedure: A mixture of 16.2 g (68 mMols) of 4-octylbenzyl chloride, 41,8 g (0.43 mols) of potassium acetate and 200 ml of glacial acetic acid was heated for 20 h to 130° C. After cooling, the mixture was poured into approximately 1 liter of water and the aqueous phase was extracted with tert.-butyl methyl ether. The organic phase was washed twice with water, repeatedly with potassium hydrogen carbonate solution (2N) and then with saturated sodium chloride solution. After the solvent had been distilled off, the residue was taken up in 160 ml of 1,2-dimethoxyethane and, after the addition of 64 g of sodium hydroxide in 130 ml of water, the solution was heated for 45 h to boiling point. After the solvent had been distilled off, the residue was extracted with tert.-butyl methyl ether, the ether phase was washed with water, the solvent was distilled off, the residue was taken up in petroleum ether and the solution was reconcentrated by evaporation after treatment with active carbon and fuller's earth. Fractionation under reduced pressure produced 8 g (54% of theoretical) of 4-octylbenzyl alcohol boiling at 128° C./0.11 mbar and having a refractive index n of 1.5033. was heated for 20 h to 130° C After cooling the aqueous phase was extracted with tert.-butyl methyl ether The organic phase was washed twice with water, repeatedly with potassium hydrogen carbonate solution (2N) After the solvent had been distilled off after the addition of 64 g of sodium hydroxide in 130 ml of water the solution was heated for 45 h After the solvent had been distilled off the residue was extracted with tert.-butyl methyl ether the ether phase was washed with water the solvent was distilled off the solution was reconcentrated by evaporation after treatment with active carbon and fuller's earth