1,1,4,4,6-pentamethyl-2,3-dihydronaphthalene

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a suspension of aluminum chloride (0.96 g, 7.17 mmol) in 1 mL of 1,2-dichloroethane under argon at room temperature was added a solution of 1,2,3,4-tetrahydro-1,1,4,4,6-pentamethylnaphthalene 29 (1.2 g, 5.93 mmol) and acetyl chloride (0.51 g, 6.52 mmol) in 9 mL of 1,2-dichloroethane. The reaction mixture was stirred for 1 h and then was poured onto ice water and extracted with 40% ethyl acetate/hexane. The combined organic layers were washed with saturated aqueous NaHCO3 and brine. The solution was. dried over anhydrous MgSO4, filtered through a plug of silica gel, and concentrated to afford a white solid 39 (1.45 g, 99%): m.p. 54°-57° C.; Rf 0.62 (10% ethyl acetate/hexane). The structure of the product was also confirmed using IR, 1H NMR and mass spectroscopy. was poured onto ice water extracted with 40% ethyl acetate/hexane The combined organic layers were washed with saturated aqueous NaHCO3 and brine dried over anhydrous MgSO4 filtered through a plug of silica gel concentrated

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

Procedure: 2,5-Dichloro-2,5-dimethylhexane (67.5 g, 0.369 mol) was dissolved in dry toluene (200 ml), and then AlCl3 (4.05 g, 30.4 mmol) was crushed up and added portionwise to the solution. After being left for 2 hours, the reaction mixture was poured into ice/5% HCl and the mixture was extracted with hexane. The organic layer was washed each twice with water, aqueous sodium hydrogen carbonate, and then with water, dried over MgSO4, and the solvent was removed by evaporation. The residue was distilled to give 5,6,7,8-tetrahydro-2,5,5,8,8-pentamethylnaphthalene (70.42 g, yield: 90%). bp 100° C. (solidified at room temperature). added portionwise to the solution the mixture was extracted with hexane The organic layer was washed each twice with water, aqueous sodium hydrogen carbonate with water, dried over MgSO4 the solvent was removed by evaporation The residue was distilled

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

Procedure: 2,5-Dichloro-2,5-dimethylhexane (67.5 g, 0.369 mol) was dissolved in dry toluene (200 ml), and then AlCl3 (4.05 g, 30.4 mmol) was crushed up and added portionwise to the solution. After being left for 2 hours, the reaction mixture was poured into ice/5% HCl and the mixture was extracted with hexane. The organic layer was washed each twice with water, aqueous sodium hydrogen carbonate, and then with water, dried over MgSO4, and the solvent was removed by evaporation. The residue was distilled to give 5,6,7,8-tetrahydro-2,5,5,8,8-pentamethylnaphthalene (70.42 g, yield: 90%). bp 100° C. (solidified at room temperature). added portionwise to the solution the mixture was extracted with hexane The organic layer was washed each twice with water, aqueous sodium hydrogen carbonate with water, dried over MgSO4 the solvent was removed by evaporation The residue was distilled

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

Procedure: 50 g (250 mmoles) of 2-methyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl naphthalene are dissolved in 200 ml of acetic anhydride. The solution is cooled to 0° C. and there is slowly added a solution of 10.5 ml (250 mmoles) of nitric acid, 20 ml of acetic acid and 20 ml of acetic anhydride, while maintaining the temperature between 0° and 5° C. The reaction mixture is then stirred for 1 hour at ambient temperature, poured into ice water and filtered. The resulting solid is washed with water. The solid is dissolved in methylene chloride, washed with water and then with a saturated solution of sodium bicarbonate, dried on MgSO4 and evaporated. 45.8 g (74%) of 2-methyl-3-nitro-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl naphthalene which melts at 143°-144° C. are obtained. while maintaining the temperature between 0° and 5° C filtered The resulting solid is washed with water The solid is dissolved in methylene chloride washed with water with a saturated solution of sodium bicarbonate, dried on MgSO4 evaporated

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

Procedure: In a round bottom flask there are introduced 64 ml (600 mmoles) of toluene and 36.6 g (200 mmoles) of 2,5-dichloro-2,5dimethyl hexane. The reaction mixture is cooled to 0° C. and there are added, by small amounts, 4.1 g (30 mmoles) of aluminum chloride. The reaction mixture is stirred for 1 hour at ambient temperature, poured into water and extracted with CH2Cl2. The organic phase is decanted, dried on magnesium sulfate and evaporated. The resulting oil is purified by distillation. 39.4 g (98%) of 2-methyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl naphthalene which boils at 68° C. (under 1 mm of mercury) are obtained. extracted with CH2Cl2 The organic phase is decanted dried on magnesium sulfate evaporated The resulting oil is purified by distillation

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

Procedure: In a round bottom flask there are introduced 64 ml (600 mmoles) of toluene and 36.6 g (200 mmoles) of 2,5-dichloro-2,5dimethyl hexane. The reaction mixture is cooled to 0° C. and there are added, by small amounts, 4.1 g (30 mmoles) of aluminum chloride. The reaction mixture is stirred for 1 hour at ambient temperature, poured into water and extracted with CH2Cl2. The organic phase is decanted, dried on magnesium sulfate and evaporated. The resulting oil is purified by distillation. 39.4 g (98%) of 2-methyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl naphthalene which boils at 68° C. (under 1 mm of mercury) are obtained. extracted with CH2Cl2 The organic phase is decanted dried on magnesium sulfate evaporated The resulting oil is purified by distillation

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

Procedure: To a suspension of AlCl3 (2.88 g; 21.6 mmol) in methylene chloride (5 ml) was added over 15 minutes a solution of 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydro-naphthalene (4.0 g; 20 mmol) and acetyl chloride (1.6 ml; 21.6 mmol) in methylene chloride (20 ml) at 0° C. The reaction mixture was stirred for 30 minutes and ice cooled water (50 ml) was added. The organic phase was separated and the water phase was further extracted with methylene chloride (3×30 ml). The combined organic phases were first washed with brine then dried before evaporated. The residue was purified by column chromatography using hexane:methylene chloride (1:1) to give the title compound in 4.9 g (100%) yield. was added The organic phase was separated the water phase was further extracted with methylene chloride (3×30 ml) The combined organic phases were first washed with brine then dried before evaporated The residue was purified by column chromatography

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

Procedure: 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (2 g, 9.9 mmol) and 4-bromobenzoyl chloride (2.17 g, 9.9 mol) were dissolved in 20 mL of CH2Cl2 and cooled to 0° C. using an ice-water-NaCl bath. AlCl3 (3.95 g, 29.7 mmol) was added in portions at over 5 min. The dark reaction mixture was allowed to stir at 0° C. for 5 min. The reaction was quenched by slow addition of ice at 0° C. The mixture was diluted with water and 150 mL of EtOAc was added and the layers were separated. The aqueous layer was washed with additional EtOAc (150 mL). The combined organic layers were washed with water (200 mL) and brine (100 mL) and dried over MgSO4. The filtrate was concentrated in vacuo to yield a yellow foamy solid residue that was recrystallized from MeOH (40 mL). The dark reaction mixture The reaction was quenched by slow addition of ice at 0° C The mixture was diluted with water and 150 mL of EtOAc was added the layers were separated The aqueous layer was washed with additional EtOAc (150 mL) The combined organic layers were washed with water (200 mL) and brine (100 mL) dried over MgSO4 The filtrate was concentrated in vacuo to yield a yellow foamy solid residue that was recrystallized from MeOH (40 mL)

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

Procedure: 1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (2 g, 9.9 mmol) and 4-bromobenzoyl chloride (2.17 g, 9.9 mol) were dissolved in 20 mL of CH2Cl2 and cooled to 0° C. using an ice-water-NaCl bath. AlCl3 (3.95 g, 29.7 mmol) was added in portions at over 5 min. The dark reaction mixture was allowed to stir at 0° C. for 5 min. The reaction was quenched by slow addition of ice at 0° C. The mixture was diluted with water and 150 mL of EtOAc was added and the layers were separated. The aqueous layer was washed with additional EtOAc (150 mL). The combined organic layers were washed with water (200 mL) and brine (100 mL) and dried over MgSO4. The filtrate was concentrated in vacuo to yield a yellow foamy solid residue that was recrystallized from MeOH (40 mL). The dark reaction mixture The reaction was quenched by slow addition of ice at 0° C The mixture was diluted with water and 150 mL of EtOAc was added the layers were separated The aqueous layer was washed with additional EtOAc (150 mL) The combined organic layers were washed with water (200 mL) and brine (100 mL) dried over MgSO4 The filtrate was concentrated in vacuo to yield a yellow foamy solid residue that was recrystallized from MeOH (40 mL)

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

Procedure: To a suspension of aluminum chloride (0.96 g, 7.17 mmol) in 1 mL of 1,2-dichloroethane under argon at room temperature was added a solution of 1,2,3,4-tetrahydro-1,1,4,4,6-pentamethylnaphthalene 29 (1.2 g, 5.93 mmol) and acetyl chloride (0.51 g, 6.52 mmol) in 9 mL of 1,2-dichloroethane. The reaction mixture was stirred for 1 h and then was poured onto ice water and extracted with 40% ethyl acetate/hexane. The combined organic layers were washed with saturated aqueous NaHCO3 and brine. The solution was. dried over anhydrous MgSO4, filtered through a plug of silica gel, and concentrated to afford a white solid 39 (1.45 g, 99%): m.p. 54°-57° C.; Rf 0.62 (10% ethyl acetate/hexane). The structure of the product was also confirmed using IR, 1H NMR and mass spectroscopy. was poured onto ice water extracted with 40% ethyl acetate/hexane The combined organic layers were washed with saturated aqueous NaHCO3 and brine dried over anhydrous MgSO4 filtered through a plug of silica gel concentrated