2-(2-methylphenyl)ethyl methanesulfonate

Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 10 g (0.0734 mol) of 2-methylphenethyl alcohol were dissolved in 200 mL of dry CH2Cl2 under a nitrogen atmosphere; the solution was cooled to 5° C., 16.4 mL (0.1175 mol) of triethylamine were added, followed by a solution of 9.1 mL (0.1175 mol) of methanesulfonyl chloride in 100 mL of dry CH2Cl2, keeping the temperature below 15° C. The reaction mixture was allowed to warm to room temperature in 2 h, then 250 mL of water were added, the organic phase was collected and the solvent was removed in vacuo. The resulting oil was taken up in Et2O and washed with 1N HCl and successively with saturated NaHCO3 solution, the solvent was removed in vacuo, yielding 14.5 g of the title product which was used without further purification. the temperature below 15° C to warm to room temperature in 2 h the organic phase was collected the solvent was removed in vacuo washed with 1N HCl and successively with saturated NaHCO3 solution the solvent was removed in vacuo

Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 10 g (0.0734 mol) of 2-methylphenethyl alcohol were dissolved in 200 mL of dry CH2Cl2 under a nitrogen atmosphere; the solution was cooled to 5° C., 16.4 mL (0.1175 mol) of triethylamine were added, followed by a solution of 9.1 mL (0.1175 mol) of methanesulfonyl chloride in 100 mL of dry CH2Cl2, keeping the temperature below 15° C. The reaction mixture was allowed to warm to room temperature in 2 h, then 250 mL of water were added, the organic phase was collected and the solvent was removed in vacuo. The resulting oil was taken up in Et2O and washed with 1N HCl and successively with saturated NaHCO3 solution, the solvent was removed in vacuo, yielding 14.5 g of the title product which was used without further purification. the temperature below 15° C to warm to room temperature in 2 h the organic phase was collected the solvent was removed in vacuo washed with 1N HCl and successively with saturated NaHCO3 solution the solvent was removed in vacuo

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

Procedure: 33.9 mL (0.223 mol) of diethyl malonate were added, under a nitrogen atmosphere and at room temperature, to a solution of sodium ethoxide (prepared in situ by dissolving 2.6 g (0.0151 mol) of Na in 80 mL of absolute EtOH). After 30 min, 14.5 g (0.0677 mol) of 2-methylphenethyl alcohol methanesulphonate dissolved in 40 mL of abs. EtOH were added dropwise and the resulting solution was heated to reflux for 3 h. EtOH was removed in vacuo, the residue was taken up in water and extracted with Et2O. The organic phase was washed successively with 10% HCl and brine, dried and the solvent was removed in vacuo. The excess diethyl malonate was removed by distillation under reduced pressure. The resulting oil (15.6 g) was used without further purification. the resulting solution was heated to reflux for 3 h EtOH was removed in vacuo extracted with Et2O The organic phase was washed successively with 10% HCl and brine dried the solvent was removed in vacuo The excess diethyl malonate was removed by distillation under reduced pressure The resulting oil (15.6 g) was used without further purification

Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 10 g (0.0734 mol) of 2-methylphenethyl alcohol were dissolved in 200 mL of dry CH2Cl2 under a nitrogen atmosphere; the solution was cooled to 5° C., 16.4 mL (0.1175 mol) of triethylamine were added, followed by a solution of 9.1 mL (0.1175 mol) of methanesulphonyl chloride in 100 mL of dry CH2Cl2, keeping the temperature below 15° C. The reaction mixture was allowed to warm to room temperate in 2 h, then 250 mL of water were added, the organic phase was collected and the solvent was removed in vacuo. The resulting oil was taken up in Et2O, the organic phase was washed with 1N HCl and with saturated NaHCO3 solution, then it was dried and the solvent was removed in vacuo, yielding 14.5 g of the title product which was used without further purification. the temperature below 15° C to warm to room temperate in 2 h the organic phase was collected the solvent was removed in vacuo the organic phase was washed with 1N HCl and with saturated NaHCO3 solution it was dried the solvent was removed in vacuo

Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 10 g (0.0734 mol) of 2-methylphenethyl alcohol were dissolved in 200 mL of dry CH2Cl2 under a nitrogen atmosphere; the solution was cooled to 5° C., 16.4 mL (0.1175 mol) of triethylamine were added, followed by a solution of 9.1 mL (0.1175 mol) of methanesulfonyl chloride in 100 mL of dry CH2Cl2, keeping the temperature below 15° C. The reaction mixture was allowed to warm to room temperature in 2 h, then 250 mL of water were added, the organic phase was collected and the solvent was removed in vacuo. The resulting oil was taken up in Et2O and washed with 1N HCl and successively with saturated NaHCO3 solution, the solvent was removed in vacuo, yielding 14.5 g of the title product which was used without further purification. the temperature below 15° C to warm to room temperature in 2 h the organic phase was collected the solvent was removed in vacuo washed with 1N HCl and successively with saturated NaHCO3 solution the solvent was removed in vacuo