7-methyloctan-1-ol

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

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

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

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: n-decylalcohol, iso-decylalcohol

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 7-methyl-octan-1-ol (1.20 g, 8.33 mmol) in DMF (20 mL) was added triphenylphosphine (2.43 g, 9.26 mmol). The solution was cooled to 0° C. and NBS (1.60 g, 8.99 mmol) was added in portions. After stirring for 30 min at room temperature, the reaction was quenched with methanol (1 mL). The solution was diluted with ether (100 mL), washed with water, saturated aqueous NaHCO3 and brine successively. The organic layer was dried and concentrated. The residue was purified by flash chromatography on silica gel, eluting with hexane to afford 1-bromo-7-methyl-octane (1.28 g, 74%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 3.41 (2H, t, J=6.6 Hz), 1.85 (2H, m), 1.52 (1H, m), 1.42 (2H, m), 1.28 (4H, m), 1.17 (2H, m), 0.87 (3H, s), 0.85 (3H, s); 13C NMR (75 MHz, CDCl3) δ 39.16, 34.34, 33.14, 29.34, 28.52, 28.24, 27.51, 22.94. the reaction was quenched with methanol (1 mL) The solution was diluted with ether (100 mL) washed with water, saturated aqueous NaHCO3 and brine successively The organic layer was dried concentrated The residue was purified by flash chromatography on silica gel eluting with hexane

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

Procedure: A solution of 7-methyl-oct-6-en-1-ol (1.42 g, 10.0 mmol) in MeOH (70 mL) was hydrogenated with Pd—C (0.40 g, 10% w/w) in a Parr apparatus at 50 psi of H2 overnight. The catalyst was removed by filtration, and the filtrate was evaporated under reduced pressure to give 7-methyl-octan-1-ol (1.38 g, 96%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 3.64 (2H, t, J=6.6 Hz), 1.54 (3H, m), 1.10–1.44 (8H, m), 0.88 (3H, s), 0.85 (3H, s); 13C NMR (75 MHz, CDCl3) δ 63.28, 39.21, 33.06, 29.98, 28.24, 27.64, 26.06, 22.94. The catalyst was removed by filtration the filtrate was evaporated under reduced pressure

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

Procedure: n-decylalcohol, iso-decylalcohol

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 7-methyl-octan-1-ol (1.20 g, 8.33 mmol) in DMF (20 mL) was added triphenylphosphine (2.43 g, 9.26 mmol). The solution was cooled to 0° C. and NBS (1.60 g, 8.99 mmol) was added in portions. After stirring for 30 min at room temperature, the reaction was quenched with methanol (1 mL). The solution was diluted with ether (100 mL), washed with water, saturated aqueous NaHCO3 and brine successively. The organic layer was dried and concentrated. The residue was purified by flash chromatography on silica gel, eluting with hexane to afford 1-bromo-7-methyl-octane (1.28 g, 74%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 3.41 (2H, t, J=6.6 Hz), 1.85 (2H, m), 1.52 (1H, m), 1.42 (2H, m), 1.28 (4H, m), 1.17 (2H, m), 0.87 (3H, s), 0.85 (3H, s); 13C NMR (75 MHz, CDCl3) δ 39.16, 34.34, 33.14, 29.34, 28.52, 28.24, 27.51, 22.94. the reaction was quenched with methanol (1 mL) The solution was diluted with ether (100 mL) washed with water, saturated aqueous NaHCO3 and brine successively The organic layer was dried concentrated The residue was purified by flash chromatography on silica gel eluting with hexane

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

Procedure: A solution of 7-methyl-oct-6-en-1-ol (1.42 g, 10.0 mmol) in MeOH (70 mL) was hydrogenated with Pd—C (0.40 g, 10% w/w) in a Parr apparatus at 50 psi of H2 overnight. The catalyst was removed by filtration, and the filtrate was evaporated under reduced pressure to give 7-methyl-octan-1-ol (1.38 g, 96%) as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 3.64 (2H, t, J=6.6 Hz), 1.54 (3H, m), 1.10–1.44 (8H, m), 0.88 (3H, s), 0.85 (3H, s); 13C NMR (75 MHz, CDCl3) δ 63.28, 39.21, 33.06, 29.98, 28.24, 27.64, 26.06, 22.94. The catalyst was removed by filtration the filtrate was evaporated under reduced pressure

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

Procedure: 976 g of benzoic acid (8 mol), 1728 g of isononanol from OXENO Olefinchemie GmbH (12 mol), and 0.59 g of butyl titanate (0.06%, based on the amount of acid) are weighed into a four liter distillation flask on top of which a water separator and reflux condenser have been attached, and which has a sampling port and thermometer, and are heated to boiling under nitrogen. The water of reaction produced during the esterification process was removed sequentially. Once the acid value fell below 0.1 mg KOH/g (after about 3 hours), the mixture was first cooled below 60° C., and a 20 cm multifill column was placed on the apparatus. The pressure was then reduced to 2 mbar, and excess alcohol was first distilled off (about 120° C.). After removal of an intermediate fraction at up to 140° C. it was possible to distill over the isononyl benzoate within a range of 142 to 147° C. (at 2 mbar) measured at the head of the column. Purity >99.7% was determined by gas chromatography. are weighed into a four liter distillation flask on top of which a water separator reflux condenser are heated The water of reaction produced during the esterification process was removed sequentially (after about 3 hours) the mixture was first cooled below 60° C. was first distilled off (about 120° C.) After removal of an intermediate fraction at up to 140° C. it to distill over the isononyl benzoate within a range of 142 to 147° C. (at 2 mbar)