3-(4-propylphenyl)propanal

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A reaction flask was charged with 3-(4-propyl-phenyl)-propionaldehyde (240 g, prepared as above), methanol (200 mL), and TMOF (150 g). The reaction mass was cooled to 0° C. and hydrochloric acid (37%, 1 g) was added in one portion. The reaction was exothermic and the temperature rose to 23° C. The reaction mass was quenched with sodium methoxide in methanol (25%, 10 g) and the solvent was removed by evaporation. The crude intermediate product 3-(4-propyl-phenyl)-propionaldehyde dimethylacetal (300 g), 2-propanol (100 mL), and rutheniium on alumina (3 g) were then charged to a 1 L zipper autoclave. The autoclave was purged with nitrogen followed by hydrogen. The autoclave was pressurized with 500 psi hydrogen and heated to 150° C. for 6 hours. The autoclave vessel was then cooled to an ambient temperature, depressurized, and purged with nitrogen. The reaction mass was filtered through celite to remove the catalyst and further hydrolyzed in the presence of water (2 L) containing hydrochloric acid (37%, 2 g) at 90° C. for 5 hours. The organic layer was separated and washed with saturated sodium carbonate solution (500 mL). Subsequent fractional distillation afforded 4-propyl cyclohexanepropanal (188 g), which had a boiling point of 107° C. at a pressure of 7 mmHg rose to 23° C The reaction mass was quenched with sodium methoxide in methanol (25%, 10 g) the solvent was removed by evaporation The crude intermediate product 3-(4-propyl-phenyl)-propionaldehyde dimethylacetal (300 g), 2-propanol (100 mL), and rutheniium on alumina (3 g) were then charged to a 1 L zipper autoclave The autoclave was purged with nitrogen heated to 150° C. for 6 hours The autoclave vessel was then cooled to an ambient temperature purged with nitrogen The reaction mass was filtered through celite to remove the catalyst further hydrolyzed in the presence of water (2 L) containing hydrochloric acid (37%, 2 g) at 90° C. for 5 hours The organic layer was separated washed with saturated sodium carbonate solution (500 mL) Subsequent fractional distillation

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A reaction flask was charged with 3-(4-propyl-phenyl)-propionaldehyde (147 g, prepared as above), methanol (500 mL), and TMOF (90 g). The reaction mass was cooled to 0° C. and hydrochloric acid (37%, 1 g) was added in one portion. The reaction was exothermic and the temperature rose to 23° C. The reaction mass was quenched with sodium methoxide in methanol (25%, 10 g) and the solvent was removed by evaporation. The crude intermediate product 3-(4-propyl-phenyl)-propionaldehyde dimethylacetal was provided and confirmed by the NMR analysis. 3-(4-Propyl-phenyl)-propionaldehyde dimethylacetal was further treated with phosphoric acid (10 g) and pyridine (8 g) at 200° C. The reaction mass was aged for 4 hours, during which methanol was recovered in a Dean Stark trap. The reaction mass was then cooled and washed with aqueous sodium carbonate solution. Fractional distillation of the organic layer afforded the product 4-propyl 1-(3-methoxy-2-propen-1-yl)benzene (80 g), which had a boiling point of 101° C. at a pressure of 3 mmHg. rose to 23° C The reaction mass was quenched with sodium methoxide in methanol (25%, 10 g) the solvent was removed by evaporation

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A reaction flask was charged with 3-(4-propyl-phenyl)-propionaldehyde (240 g, prepared as above), methanol (200 mL), and TMOF (150 g). The reaction mass was cooled to 0° C. and hydrochloric acid (37%, 1 g) was added in one portion. The reaction was exothermic and the temperature rose to 23° C. The reaction mass was quenched with sodium methoxide in methanol (25%, 10 g) and the solvent was removed by evaporation. The crude intermediate product 3-(4-propyl-phenyl)-propionaldehyde dimethylacetal (300 g), 2-propanol (100 mL), and rutheniium on alumina (3 g) were then charged to a 1 L zipper autoclave. The autoclave was purged with nitrogen followed by hydrogen. The autoclave was pressurized with 500 psi hygrogen and heated to 150° C. for 6 hours. The autoclave vessel was then cooled to an ambient temperature, depressurized, and purged with nitrogen. The reaction mass was filtered through celite to remove the catalyst and further hydrolyzed in the presence of water (2 L) containing hydrochloric acid (37%, 2 g) at 90° C. for 5 hours. The organic layer was separated and washed with saturated sodium carbonate solution (500 mL). Subsequent fractional distillation afforded 4-propyl cyclohexanepropanal (188 g), which had a boiling point of 107° C. at a pressure of 7 mmHg. rose to 23° C The reaction mass was quenched with sodium methoxide in methanol (25%, 10 g) the solvent was removed by evaporation The crude intermediate product 3-(4-propyl-phenyl)-propionaldehyde dimethylacetal (300 g), 2-propanol (100 mL), and rutheniium on alumina (3 g) were then charged to a 1 L zipper autoclave The autoclave was purged with nitrogen heated to 150° C. for 6 hours The autoclave vessel was then cooled to an ambient temperature purged with nitrogen The reaction mass was filtered through celite to remove the catalyst further hydrolyzed in the presence of water (2 L) containing hydrochloric acid (37%, 2 g) at 90° C. for 5 hours The organic layer was separated washed with saturated sodium carbonate solution (500 mL) Subsequent fractional distillation