2-tert-butylcyclohexa-2,5-diene-1,4-dione

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

Procedure: Hexachlorocyclopentadiene, 40 g., and 15.4 g. of tert-butyl-p-benzoquinone were dissolved in 300 ml. of toluene and refluxed for four hours. The solution solidified upon cooling to room temperature. The solid was washed with methanol and recrystallized from benzene. Yellow crystals were obtained, melting at 124° -125° C. The solid was washed with methanol recrystallized from benzene Yellow crystals were obtained

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

Procedure: 30 g. of tert-butylhydroquinone (Eastman-Kodak) were dissolved in 200 ml. of anhydrous ether and 30 g. of anhydrous sodium sulfate were added. To this mixture was added 60 g. of silver oxide in small increments. An exothermic reaction ensued. After shaking for 20 minutes, the reaction mixture was filtered and the filtrate evaporated under the hood. Yellow crystals of tert-butyl-p-benzoquinone were obtained melting at 55° -60° C. To this mixture was added 60 g An exothermic reaction the reaction mixture was filtered the filtrate evaporated under the hood

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

Procedure: 30 g. of tert-butylhydroquinone (Eastman-Kodak) were dissolved in 200 ml. of anhydrous ether and 30 g. of anhydrous sodium sulfate were added. To this mixture was added 60 g. of silver oxide in small increments. An exothermic reaction ensued. After shaking for 20 minutes, the reaction mixture was filtered and the filtrate evaporated under the hood. Yellow crystals of tert-butyl-p-benzoquinone were obtained melting at 55° -60° C. To this mixture was added 60 g An exothermic reaction the reaction mixture was filtered the filtrate evaporated under the hood

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 16.6 g (0.10 mol) of 2-tert-butylhydroquinone was placed in a 200 cc 3-neck flask. After adding 17.4 g (0.20 mol) of powdery manganese dioxide, 100 cc of toluene was added thereto, and the mixture was heated with stirring. The temperature was maintained at 70° C. for 3 hours. After cooling to room temperature, the manganese dioxide was removed by filtration by means of suction using Celite as a filter aid. Then the manganese dioxide was washed with 50 cc of toluene, and the toluene was evaporated to dryness, by which 2-tert-butyl-1,4-benzoquinone was obtained. The yield was 80% and the melting point was 48°-50° C. was added the mixture was heated After cooling to room temperature the manganese dioxide was removed by filtration by means of suction Then the manganese dioxide was washed with 50 cc of toluene the toluene was evaporated to dryness, by which 2-tert-butyl-1,4-benzoquinone was obtained

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

Procedure: Hexachlorocyclopentadiene, 40 g., and 15.4 g. of tert-butyl-p-benzoquinone were dissolved in 300 ml. of toluene and refluxed for four hours. The solution solidified upon cooling to room temperature. The solid was washed with methanol and recrystallized from benzene. Yellow crystals were obtained melting at 124°-125° C. The solid was washed with methanol recrystallized from benzene Yellow crystals were obtained melting at 124°-125° C.

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

Procedure: 30 g. of tert-butylhydroquinone (Eastman-Kodak) were dissolved in 200 ml. of anhydrous ether and 30 g. of anhydrous sodium sulfate were added. To this mixture was added 60 g. of silver oxide in small increments. An exothermic reaction ensued. After shaking for 20 minutes, the reaction mixture was filtered and the filtrate evaporated under the hood. Yellow crystals of tert-butyl-p-benzoquinone were obtained melting at 55°-60° C. To this mixture was added 60 g An exothermic reaction the reaction mixture was filtered the filtrate evaporated under the hood

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 16.6 g (0.10 mol) of 2-tert-butylhydroquinone was placed in a 200 cc 3-neck flask. After adding 17.4 g (0.20 mol) of powdery manganese dioxide, 100 cc of toluene was added thereto, and the mixture was heated with stirring. The temperature was maintained at 70° C. for 3 hours. After cooling to room temperature, the manganese dioxide was removed by filtration by means of suction using Celite as a filter aid. Then the manganese dioxide was washed with 50 cc of toluene, and the toluene was evaporated to dryness, by which 2-tert-butyl-1,4-benzoquinone was obtained. The yield was 80% and the melting point was 48°-50° C. was added the mixture was heated After cooling to room temperature the manganese dioxide was removed by filtration by means of suction Then the manganese dioxide was washed with 50 cc of toluene the toluene was evaporated to dryness, by which 2-tert-butyl-1,4-benzoquinone was obtained

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

Procedure: Hexachlorocyclopentadiene, 40 g., and 15.4 g. of tert-butyl-p-benzoquinone were dissolved in 300 ml. of toluene and refluxed for four hours. The solution solidified upon cooling to room temperature. The solid was washed with methanol and recrystallized from benzene. Yellow crystals were obtained melting at 124°-125° C. The solid was washed with methanol recrystallized from benzene Yellow crystals were obtained melting at 124°-125° C.

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

Procedure: 30 g. of tert-butylhydroquinone (Eastman-Kodak) were dissolved in 200 ml. of anhydrous ether and 30 g. of anhydrous sodium sulfate were added. To this mixture was added 60 g. of silver oxide in small increments. An exothermic reaction ensued. After shaking for 20 minutes, the reaction mixture was filtered and the filtrate evaporated under the hood. Yellow crystals of tert-butyl-p-benzoquinone were obtained melting at 55°-60° C. To this mixture was added 60 g An exothermic reaction the reaction mixture was filtered the filtrate evaporated under the hood

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 80 mmol t-butylhydroquinone together with 80 mmol potassium bromate is suspended in 100 ml water. 20 drops 1 M sulfuric acid is added thereto while stirring. The reaction mixture is slowly heated to 80° C. while stirring. A clear orange solution of the quinone forms. When this is cooled to room temperature orange needles precipitate (t-butylbenzoquinone). These are dissolved in 400 ml ethanol while still wet. The solution is irradiated for 15 h at 5° C. with a 250 W sodium-vapour lamp (TLC control). The solvent is removed by distillation, the residue is washed with toluene/hexane 1:1. The remaining colourless crystalline residue (2-(2'-ethyl-2'-ethoxy-propyl)-hydroquinone) is fed into a mixture of 4 ml ethanol and 80 ml glacial acetic acid. 4 ml 40% aqueous tetrafluoroboric acid is added while stirring. The mixture is heated to 80° C. during which a clear solution forms. After cooling to room temperature it is poured onto 200 ml water and extracted with toluene. The organic phase is washed once with water and dried over potassium carbonate. After removing the solvent by distillation an oil remains (5-hydroxy-2,2-dimethyl-2,3-dihydro-benzofurane). The benzoylation, oxidation and saponification are carried out as described in example 15. while stirring The solvent is removed by distillation the residue is washed with toluene/hexane 1:1 The remaining colourless crystalline residue (2-(2'-ethyl-2'-ethoxy-propyl)-hydroquinone) is fed into a mixture of 4 ml ethanol and 80 ml glacial acetic acid 4 ml 40% aqueous tetrafluoroboric acid is added while stirring The mixture is heated to 80° C. during which a clear solution forms After cooling to room temperature it is poured onto 200 ml water extracted with toluene The organic phase is washed once with water dried over potassium carbonate After removing the solvent by distillation an oil

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

Procedure: Hexachlorocyclopentadiene, 40 g., and 15.4 g. of tert-butyl-p-benzoquinone were dissolved in 300 ml. of toluene and refluxed for four hours. The solution solidified upon cooling to room temperature. The solid was washed with methanol and recrystallized from benzene. Yellow crystals were obtained, melting at 124°-125° C. The solid was washed with methanol recrystallized from benzene Yellow crystals were obtained

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

Procedure: 30 g. of tert-butylhydroquinone (Eastman-Kodak) were dissolved in 200 ml. of anhydrous ether and 30 g. of anhydrous sodium sulfate were added. To this mixture was added 60 g. of silver oxide in small increments. An exothermic reaction ensued. After shaking for 20 minutes, the reaction mixture was filtered and the filtrate evaporated under the hood. Yellow crystals of tert-butyl-p-benzoquinone were obtained melting at 55°-60° C. To this mixture was added 60 g An exothermic reaction the reaction mixture was filtered the filtrate evaporated under the hood