3,5-dimethyl-4-nitrosophenol

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

Procedure: 750 ml of concentrated HCl are added to a solution of 3,5-dimethyl phenol (80.6 g) in 750 ml of 95% ethyl alcohol. The mixture is cooled to 0° C. in an ice/methanol bath. While maintaining the temperature of the reaction mixture below 5° C., a solution of NaNO2 (69.0 g) in 150 ml of H2O is added dropwise to the reaction mixture. The mixture is stirred at 0° C. for more than an hour and then poured into 9 liters of water. The aqueous mixture is filtered to give a yellow solid which is recrystallized from hot methanol and filtered to give 71.45 grams of a yellow solid, M.P. 180°-181° C. (dec). While maintaining the temperature of the reaction mixture below 5° C. The aqueous mixture is filtered to give a yellow solid which is recrystallized from hot methanol filtered

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

Procedure: 750 ml of concentrated HCl are added to a solution of 3,5-dimethyl phenol (80.6 g) in 750 ml of 95% ethyl alcohol. The mixture is cooled to 0° C. in an ice/methanol bath. While maintaining the temperature of the reaction mixture below 5° C., a solution of NaNO2 (69.0 g) in 150 ml of H2O is added dropwise to the reaction mixture. The mixture is stirred at 0° C. for more than an hour and then poured into 9 liters of water. The aqueous mixture is filtered to give a yellow solid which is recrystallized from hot methanol and filtered to give 71.45 grams of a yellow solid, M.P. 180°-181° C. (dec). While maintaining the temperature of the reaction mixture below 5° C. The aqueous mixture is filtered to give a yellow solid which is recrystallized from hot methanol filtered

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3,5-dimethyl-4-nitrosophenol (70.63 g) from above and (NH4)6Mo7O24.4H2O) (2.83 g) in 770 ml of glacial acetic acid was warmed to 100° C. 30% H2O2 (84 ml) was added to the mixture in 10 ml portions until an exothermic reaction was observed. The reaction mixture was then stirred and the remainder of the H2O2 solution added in small portions. The reaction mixture was heated and stirred until a clear dark red solution results. A yellow-orange solid precipitated from the solution after stirring for another 20-30 minutes. The reaction mixture was stirred overnight and filtered to give a small amount of a yellow solid and a clear dark red filtrate. The red filtrate was concentrated in vacuo and partitioned between water and ether. The aqueous layer was washed with ether and the combined ether extracts washed with 10% sodium carbonate until the aqueous layer becomes basic. The ether extract was dried over anhydrous sodium sulfate, filtered, concentrated and allowed to cool overnight. After cooling in an ice bath the mixture was filtered to give 49.5 g of 3,5-dimethyl-4-nitrophenol as a yellow-green solid. Mp. 106-108° C. The reaction mixture was heated stirred until a clear dark red solution results A yellow-orange solid precipitated from the solution after stirring for another 20-30 minutes The reaction mixture was stirred overnight filtered to give a small amount of a yellow solid The red filtrate was concentrated in vacuo partitioned between water and ether The aqueous layer was washed with ether the combined ether extracts washed with 10% sodium carbonate until the aqueous layer The ether extract was dried over anhydrous sodium sulfate filtered concentrated to cool overnight After cooling in an ice bath the mixture was filtered

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

Procedure: [3,5-Dimethyl-4-nitrophenol was synthesized by the reference procedures (U.S. Pat. No. 4,564,640) J 750 ml of Concentrated hydrochloric acid was added to a solution of 3,5-dimethylphenol (80.6 g) in 750 ml of 95% ethanol. The mixture was cooled to 0° C. in an ice/methanol bath. While maintaining the temperature of the reaction mixture below 5° C., a solution of NaNO2 (69.0 g) in 150 ml of water was added dropwise to the reaction mixture. The mixture was stirred at 0° C. for more than an hour and then poured into 9 liters of water. The aqueous mixture was filtered to give a yellow solid which was recrystallized from hot methanol and filtered to give 71.45 g of 3,5-dimethyl-4-nitrosophenol as a yellow solid. Mp. 180-181° C. While maintaining the temperature of the reaction mixture below 5° C. The aqueous mixture was filtered to give a yellow solid which was recrystallized from hot methanol filtered

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

Procedure: [3,5-Dimethyl-4-nitrophenol was synthesized by the reference procedures (U.S. Pat. No. 4,564,640) J 750 ml of Concentrated hydrochloric acid was added to a solution of 3,5-dimethylphenol (80.6 g) in 750 ml of 95% ethanol. The mixture was cooled to 0° C. in an ice/methanol bath. While maintaining the temperature of the reaction mixture below 5° C., a solution of NaNO2 (69.0 g) in 150 ml of water was added dropwise to the reaction mixture. The mixture was stirred at 0° C. for more than an hour and then poured into 9 liters of water. The aqueous mixture was filtered to give a yellow solid which was recrystallized from hot methanol and filtered to give 71.45 g of 3,5-dimethyl-4-nitrosophenol as a yellow solid. Mp. 180-181° C. While maintaining the temperature of the reaction mixture below 5° C. The aqueous mixture was filtered to give a yellow solid which was recrystallized from hot methanol filtered

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

Procedure: 750 ml of concentrated HCl are added to a solution of 3,5-dimethyl phenol (80.6 g) in 750 ml of 95% ethyl alcohol. The mixture is cooled to 0° C. in an ice/methanol bath. While maintaining the temperature of the reaction mixture below 5° C., a solution of NaNO2 (69.0 g) in 150 ml of H2O is added dropwise to the reaction mixture. The mixture is stirred at 0° C. for more than an hour and then poured into 9 liters of water. The aqueous mixture is filtered to give a yellow solid which is recrystallized from hot methanol and filtered to give 71.45 grams of a yellow solid, M.P. 180°-181° C. (dec). While maintaining the temperature of the reaction mixture below 5° C. The aqueous mixture is filtered to give a yellow solid which is recrystallized from hot methanol filtered

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

Procedure: A mixture of 12.08 g of 3,5-dimethyl-4-nitrosophenol, 11.45 g of cuprous oxide, 100 ml of 1,4-dioxane, 10 ml of acetone and 100 ml of 6N hydrochloric acid was heated under reflux for 2 hours. The reaction mixture was poured into iced water, followed by extraction with ether. The extract was dried over anhydrous sodium sulfate and the solvent was then distilled off under reduced pressure. The residue was dissolved in 150 ml of dichloromethane. To the resulting solution, 3.61 g of sodium borohydride were added under ice cooling, followed by the dropwise addition of 50 ml of methanol at an internal temperature not higher than 10° C. The reaction mixture was stirred at room temperature for 90 minutes. The reaction mixture was concentrated by evaporation. The concentrate was poured into iced water. The resulting mixture was acidified with 3N hydrochloric acid. The precipitated product was collected by filtration, washed successively with water and n-hexane, whereby 5.93 g of the title compound were obtained. was heated under reflux for 2 hours followed by extraction with ether The extract was dried over anhydrous sodium sulfate the solvent was then distilled off under reduced pressure The residue was dissolved in 150 ml of dichloromethane To the resulting solution, 3.61 g of sodium borohydride were added under ice cooling followed by the dropwise addition of 50 ml of methanol at an internal temperature not higher than 10° C The reaction mixture was concentrated by evaporation The concentrate was poured into iced water The precipitated product was collected by filtration washed successively with water and n-hexane

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3,5-dimethyl-4-nitrosophenol (70.63 g) from above and (NH4)6Mo7O24.4H2O) (2.83g) in 770 ml of glacial acetic acid was warmed to 100° C. 30% H2O2 (84 ml) was added to the mixture in 10 ml portions until an exothermic reaction was observed. The reaction mixture was then stirred and the remainder of the H2O2 solution added in small portions. The reaction mixture was heated and stirred until a clear dark red solution results. A yellow-orange solid precipitated from the solution after stirring for another 20-30 minutes. The reaction mixture was stirred overnight and filtered to give a small amount of a yellow solid and a clear dark red filtrate. The red filtrate was concentrated in vacuo and partitioned between water and ether. The aqueous layer was washed with ether and the combined ether extracts washed with 10% sodium carbonate until the aqueous layer becomes basic. The ether extract was dried over anhydrous sodium sulfate, filtered, concentrated and allowed to cool overnight. After cooling in an ice bath the mixture was filtered to give 49.5 g of 3,5-dimethyl-4-nitrophenol as a yellow-green solid. Mp. 106-108° C. The reaction mixture was heated stirred until a clear dark red solution results A yellow-orange solid precipitated from the solution after stirring for another 20-30 minutes The reaction mixture was stirred overnight filtered to give a small amount of a yellow solid The red filtrate was concentrated in vacuo partitioned between water and ether The aqueous layer was washed with ether the combined ether extracts washed with 10% sodium carbonate until the aqueous layer The ether extract was dried over anhydrous sodium sulfate filtered concentrated to cool overnight After cooling in an ice bath the mixture was filtered

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

Procedure: [3,5-Dimethyl-4-nitrophenol was synthesized by the reference procedures (U.S. Pat. No. 4,564,640)] 750 ml of Concentrated hydrochloric acid was added to a solution of 3,5-dimethylphenol (80.6 g) in 750 ml of 95% ethanol. The mixture was cooled to 0° C. in an ice/methanol bath. While maintaining the temperature of the reaction mixture below 5° C., a solution of NaNO2 (69.0 g) in 150 ml of water was added dropwise to the reaction mixture. The mixture was stirred at 0° C. for more than an hour and then poured into 9 liters of water. The aqueous mixture was filtered to give a yellow solid which was recrystallized from hot methanol and filtered to give 71.45 g of 3,5-dimethyl-4-nitrosophenol as a yellow solid. Mp. 180-181° C. While maintaining the temperature of the reaction mixture below 5° C. The aqueous mixture was filtered to give a yellow solid which was recrystallized from hot methanol filtered

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

Procedure: 750 ml of concentrated HClare added to a solution of 3,5-dimethyl phenol (80.6 g) in 750 ml of 95% ethyl alcohol. The mixture is cooled to 0° C. in an ice/methanol bath. While maintaining the temperature of the reaction mixture below 5° C. a solution of NaNO2 (69.0 g) in 150 ml of H2O is added dropwise to the reaction mixture. The mixture is stirred at 0° C. for more than an hour and then poured into 9 liters of water. The aqueous mixture is filtered to give a yellow solid which is recrystallized from hot methanol and filtered to give 71.45 grams of a yellow solid, M.P. 180°-181° C. (dec). is added dropwise to the reaction mixture The aqueous mixture is filtered to give a yellow solid which is recrystallized from hot methanol filtered

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

Procedure: 750 ml of concentrated HCl are added to a solution of 3,5-dimethyl phenol (80.6 g) in 750 ml of 95% ethyl alcohol. The mixture is cooled to 0° C. in an ice/methanol bath. While maintaining the temperature of the reaction mixture below 5° C., a solution of NaNO2 (69.0 g) in 150 ml of H2O is added dropwise to the reaction mixture. The mixture is stirred at 0° C. for more than an hour and then poured into 9 liters of water. The aqueous mixture is filtered to give a yellow solid which is recrystallized from hot methanol and filtered to give 71.45 grams of a yellow solid, M.P. 180°-181° C. (dec.). While maintaining the temperature of the reaction mixture below 5° C. The aqueous mixture is filtered to give a yellow solid which is recrystallized from hot methanol filtered

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3,5-dimethyl-4-nitrosophenol (70.63 g) from above and (NH4)6Mo7O24.4H2O) (2.83 g) in 770 ml of glacial acetic acid was warmed to 100° C. 30% H2O2 (84 ml) was added to the mixture in 10 ml portions until an exothermic reaction was observed. The reaction mixture was then stirred and the remainder of the H2O2 solution added in small portions. The reaction mixture was heated and stirred until a clear dark red solution results. A yellow-orange solid precipitated from the solution after stirring for another 20-30 minutes. The reaction mixture was stirred overnight and filtered to give a small amount of a yellow solid and a clear dark red filtrate. The red filtrate was concentrated in vacuo and partitioned between water and ether. The aqueous layer was washed with ether and the combined ether extracts washed with 10% sodium carbonate until the aqueous layer becomes basic. The ether extract was dried over anhydrous sodium sulfate, filtered, concentrated and allowed to cool overnight. After cooling in an ice bath the mixture was filtered to give 49.5 g of 3,5-dimethyl-4-nitrophenol as a yellow-green solid. Mp. 106-108° C. The reaction mixture was heated stirred until a clear dark red solution results A yellow-orange solid precipitated from the solution after stirring for another 20-30 minutes The reaction mixture was stirred overnight filtered to give a small amount of a yellow solid The red filtrate was concentrated in vacuo partitioned between water and ether The aqueous layer was washed with ether the combined ether extracts washed with 10% sodium carbonate until the aqueous layer The ether extract was dried over anhydrous sodium sulfate filtered concentrated to cool overnight After cooling in an ice bath the mixture was filtered