4-methylcyclohexene

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

Procedure: 2.0 g 5-tert-butyl-2-methoxy-1,3-dinitro-benzene are dissolved in 20 ml of ethanol, combined with 100 μl water and 100 mg of 10% palladium on activated charcoal and then refluxed. 1.9 ml of 4-methyl-cyclohexene are added and the mixture is refluxed for a further 2 hours. Then a further 950 μl of 4-methyl-cyclohexene are added dropwise and then refluxed for 16 hours. The solvents are then eliminated in vacuo, the residue is taken up in ethyl acetate and washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution. After drying with sodium sulphate the solvents are eliminated in vacuo and the residue is dried in vacuo. refluxed the mixture is refluxed for a further 2 hours refluxed for 16 hours washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution After drying with sodium sulphate the solvents the residue is dried in vacuo

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

Procedure: 2 g 5-tert-butyl-2-methoxy-1,3-dinitro-benzene are dissolved in 20 ml ethanol and combined with 2 ml of water and 100 mg of 10% palladium on charcoal. The mixture is refluxed, 1.9 ml of 4-methyl-1-cyclohexene are added and the mixture is refluxed for a further 2 hours. Then a further 1.0 ml of 4-methyl-1-cyclohexene are added dropwise and the mixture is refluxed for a further 16 hours. Then it is cooled to ambient temperature, the solvents are eliminated in vacuo and the residue is taken up in ethyl acetate. The mixture is washed with saturated aqueous sodium hydrogen carbonate solution, water, saturated aqueous sodium chloride solution and dried with sodium sulphate. The solvent is eliminated in vacuo and the product thus obtained is further reacted directly. The mixture is refluxed the mixture is refluxed for a further 2 hours the mixture is refluxed for a further 16 hours The mixture is washed with saturated aqueous sodium hydrogen carbonate solution, water, saturated aqueous sodium chloride solution dried with sodium sulphate the product thus obtained is further reacted directly

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

Procedure: 2 g 5-tert-butyl-2-methoxy-1,3-dinitro-benzene are dissolved in 20 ml ethanol and combined with 2 ml of water and 100 mg of 10% palladium on charcoal. The mixture is refluxed, 1.9 ml of 4-methyl-1-cyclohexene are added and the mixture is refluxed for a further 2 hours. Then a further 1.0 ml of 4-methyl-1-cyclohexene are added dropwise and the mixture is refluxed for a further 16 hours. Then it is cooled to ambient temperature, the solvents are eliminated in vacuo and the residue is taken up in ethyl acetate. The mixture is washed with saturated aqueous sodium hydrogen carbonate solution, water, saturated aqueous sodium chloride solution and dried with sodium sulphate. The solvent is eliminated in vacuo and the product thus obtained is further reacted directly. The mixture is refluxed the mixture is refluxed for a further 2 hours the mixture is refluxed for a further 16 hours The mixture is washed with saturated aqueous sodium hydrogen carbonate solution, water, saturated aqueous sodium chloride solution dried with sodium sulphate the product thus obtained is further reacted directly

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

Procedure: 2.0 g 5-tert-butyl-2-methoxy-1,3-dinitro-benzene are dissolved in 20 ml of ethanol, combined with 100 μl water and 100 mg of 10% palladium on activated charcoal and then refluxed. 1.9 ml of 4-methyl-cyclohexene are added and the mixture is refluxed for a further 2 hours. Then a further 950 μl of 4-methyl-cyclohexene are added dropwise and then refluxed for 16 hours. The solvents are then eliminated in vacuo, the residue is taken up in ethyl acetate and washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution. After drying with sodium sulphate the solvents are eliminated in vacuo and the residue is dried in vacuo. refluxed the mixture is refluxed for a further 2 hours refluxed for 16 hours washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution After drying with sodium sulphate the solvents the residue is dried in vacuo

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

Procedure: Under N2 was charged 4-tert-butyl-2,6-dinitroanisole (620 g, 2.439 mol), IMS (4774 mL) and 10% Pd/C (31.8 g). The reaction mixture was heated to reflux (78° C.) and 4-methyl-1-cyclohexene (500 mL, 4.159 mol) was added dropwise over 4.5 h. The reaction was stirred at reflux overnight, whereupon HPLC analysis indicated 72.13% product and 27.17% starting material. Further 4-methyl-1-cyclohexene (160 mL, 1.331 mol) was added dropwise over 3 h and the reaction was stirred at reflux for 72 h. HPLC analysis indicated 92.72% product and 0% starting material. The reaction was cooled to room temperature and the catalyst was removed via vacuum filtration and washed with IMS (500 mL). The solvents were concentrated to ca. 1200 mL to give a ratio of 1:4.45 product:ethanol (target 1:5). 2 M HCl (124 mL) was charged dropwise to the remainder while maintaining the temperature below 23° C. Water (3100 mL) was charged and the resulting suspension was stirred at room temperature for 1.5 h. The solid was collected via vacuum filtration and washed with water (2×1000 mL). The resulting orange needles were dried, under vacuum, at 40° C. overnight. Yield=475.2 g (86.9%). Purity >97% by 1H NMR. HPLC purity 98.8%. KF 0.36%. The reaction mixture was heated was added dropwise over 4.5 h at reflux overnight, whereupon HPLC analysis the reaction was stirred at reflux for 72 h the catalyst was removed via vacuum filtration washed with IMS (500 mL) The solvents were concentrated to ca. 1200 mL to give a ratio of 1:4.45 product while maintaining the temperature below 23° C the resulting suspension was stirred at room temperature for 1.5 h The solid was collected via vacuum filtration washed with water (2×1000 mL) The resulting orange needles were dried, under vacuum, at 40° C. overnight

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

Procedure: 2.0 g 5-tert-butyl-2-methoxy-1,3-dinitro-benzene are dissolved in 20 ml of ethanol, combined with 100 μl water and 100 mg of 10% palladium on activated charcoal and then refluxed. 1.9 ml of 4-methyl-cyclohexene are added and the mixture is refluxed for a further 2 hours. Then a further 950 μl of 4-methyl-cyclohexene are added dropwise and then refluxed for 16 hours. The solvents are then eliminated in vacuo, the residue is taken up in ethyl acetate and washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution. After drying with sodium sulphate the solvents are eliminated in vacuo and the residue is dried in vacuo. refluxed the mixture is refluxed for a further 2 hours refluxed for 16 hours washed successively with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution After drying with sodium sulphate the solvents the residue is dried in vacuo