2,2-dimethylpropylbenzene

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

Procedure: To a cooled suspension of 43.0 g of anhydrous aluminum chloride in 250 ml of methylene chloride was added 40.0 g of oxalyl chloride over a period of 25 minutes. The resulting mixture was stirred for 5 minutes and then 43.2 g of neopentylbenzene was added dropwise maintaining a temperature of 0°-5° C. over a period of 35 minutes. The dark red mixture was stirred at an ambient temperature and then heated slowly to reflux for 3 hours, cooled, and poured into a mixture of 250 g of ice and 188 ml of concentrated hydrochloric acid. The mixture was stirred for 1/2 hour, and two layers were separated. The aqueous layer was extracted with methylene chloride and the combined organic layers were evaporated to yield a brown oily residue. The residue was heated and stirred under reflux with 200 ml of 10N sodium hydroxide, 150 ml of water, and 250 ml of ethyl alcohol for 20 minutes, cooled, and the mixture was extracted with ether. The aqueous layer was acidified with concentrated hydrochloric acid and stirred for 1 hour. The solid was collected by filtration, washed with water, dissolved in ethyl acetate, the aqueous layer was discarded, dried and evaporated to yield a solid. The solid was crystallized from acetone to yield p-neopentylbenzoic acid as a beige solid, mp 191°-193° C. maintaining a temperature of 0°-5° C. over a period of 35 minutes The dark red mixture was stirred at an ambient temperature heated slowly to reflux for 3 hours cooled The mixture was stirred for 1/2 hour two layers were separated The aqueous layer was extracted with methylene chloride the combined organic layers were evaporated to yield a brown oily residue The residue was heated stirred cooled the mixture was extracted with ether stirred for 1 hour The solid was collected by filtration washed with water dissolved in ethyl acetate dried evaporated to yield a solid The solid was crystallized from acetone

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

Procedure: A process for the preparation of 2-neopentylanthraquinone, wherein neopentylbenzene is acylated with phthalic anhydride by a Friedel-Crafts reaction to give 2-(4-neopentylbenzoyl)-benzoic acid and the latter is cyclized in the presence of a strong anhydrous acid to give a composition consisting essentially of 2-neopentylanthraquinone without isomerization or degradation of the neopentyl group taking place.

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

Procedure: In the novel process, neopentylbenzene (1) is acylated in a first step with phthalic anhydride (2) under Friedel-Crafts conditions to give 2-(4-neopentylbenzoyl)-benzoic acid (3). ##STR3##

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

Procedure: We have found that this object is achieved by the novel compound 2-neopentylanthraquinone of the formula ##STR2## Furthermore, we have found a process for the preparation of 2-neopentylanthraquinone, wherein neopentylbenzene is acylated with phthalic anhydride by a Friedel-Crafts reaction to give 2-(4-neopentylbenzoyl)-benzoic acid and the latter is cyclized in the presence of a strong anhydrous acid to give 2-neopentylanthraquinone. We have also found that 2-neopentylanthraquinone is a catalyst for the preparation of hydrogen peroxide.

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

Procedure: The novel compound 2-neopentylanthraquinone which is prepared by Friedel-Crafts acylation of neopentylbenzene with phthalic anhydride and subsequent cyclization of the resulting 2-(4-neopentylbenzoyl)-benzoic acid in the presence of a strong, anhydrous acid, is a catalyst for the preparation of hydrogen peroxide.

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

Procedure: The novel compound 2-neopentylanthraquinone which is prepared by Friedel-Crafts acylation of neopentylbenzene with phthalic anhydride and subsequent cyclization of the resulting 2-(4-neopentylbenzoyl)-benzoic acid in the presence of a strong, anhydrous acid, is a catalyst for the preparation of hydrogen peroxide.

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

Procedure: To a cooled suspension of 43.0 g of anhydrous aluminum chloride in 250 ml of methylene chloride was added 40.0 g of oxalyl chloride over a period of 25 minutes. The resulting mixture was stirred for 5 minutes and then 43.2 g of neopentylbenzene was added dropwise maintaining a temperature of 0°-5° C. over a period of 35 minutes. The dark red mixture was stirred at an ambient temperature and then heated slowly to reflux for 3 hours, cooled, and poured into a mixture of 250 g of ice and 188 ml of concentrated hydrochloric acid. The mixture was stirred for 1/2 hour, and two layers were separated. The aqueous layer was extracted with methylene chloride and the combined organic layers were evaporated to yield a brown oily residue. The residue was heated and stirred under reflux with 200 ml of 10N sodium hydroxide, 150 ml of water, and 250 ml of ethyl alcohol for 20 minutes, cooled, and the mixture was extracted with ether. The aqueous layer was acidified with concentrated hydrochloric acid and stirred for 1 hour. The solid was collected by filtration, washed with water, dissolved in ethyl acetate, the aqueous layer was discarded, dried and evaporated to yield a solid. The solid was crystallized from acetone to yield p-neopentylbenzoic acid as a beige solid, mp 191°-193° C. maintaining a temperature of 0°-5° C. over a period of 35 minutes The dark red mixture was stirred at an ambient temperature heated slowly to reflux for 3 hours cooled The mixture was stirred for 1/2 hour two layers were separated The aqueous layer was extracted with methylene chloride the combined organic layers were evaporated to yield a brown oily residue The residue was heated stirred cooled the mixture was extracted with ether stirred for 1 hour The solid was collected by filtration washed with water dissolved in ethyl acetate dried evaporated to yield a solid The solid was crystallized from acetone

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

Procedure: (2,2-Dimethylpropyl)benzene (9.33 g, 63 mmol) was dissolved in dichloromethane (50 mL) and cooled to 0° C. on an ice bath. With vigorous stirring, SnCl4 (28.66 g, 110 mmol) was added all at once via syringe, followed by dropwise addition of dichloromethyl methyl ether (7.24 g, 63 mmol) over 10 min. After 20 min, the ice bath was removed, and the mixture was quenched by the addition of ice-water (100 mL). The aqueous layer was discarded and the organic phase was washed with water (3×25 mL), 3 N hydrochloric acid (3×25 mL), and aqueous saturated sodium chloride (2×25 mL). The organic phase was then treated with activated carbon, dried (magnesium sulphate), filtered and concentrated in vacuo. This afforded the title compound. Yield 7.49 g (62%). the ice bath was removed the mixture was quenched by the addition of ice-water (100 mL) the organic phase was washed with water (3×25 mL), 3 N hydrochloric acid (3×25 mL), and aqueous saturated sodium chloride (2×25 mL) The organic phase was then treated with activated carbon dried (magnesium sulphate) filtered concentrated in vacuo

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

Procedure: To a cooled suspension of 43.0 g of anhydrous aluminum chloride in 250 ml of methylene chloride was added 40.0 g of oxalyl chloride over a period of 25 minutes. The resulting mixture was stirred for 5 minutes and then 43.2 g of neopentylbenzene was added dropwise maintaining a temperature of 0°-50° C. over a period of 35 minutes. The dark red mixture was stirred at an ambient temperature and then heated slowly to reflux for 3 hours, cooled, and poured into a mixture of 250 g of ice and 188 ml of concentrated hydrochloric acid. The mixture was stirred for 1/2 hours, and two layers were separated. The aqueous layer was extracted with methylene chloride and the combined organic layers were evaporated to yield a brown oily residue. The residue was heated and stirred under reflux with 200 ml of 10N sodium hydroxide, 150 ml of water, and 250 ml of ethyl alcohol for 20 minutes, cooled, and the mixture was extracted with ether. The aqueous layer was acidified with concentrated hydrochloric acid and stirred for 1 hour. The solid was collected by filtration, washed with water, dissolved in ethyl acetate, the aqueous layer was discarded, dried and evaporated to yield a solid. The solid was crystallized from acetone to yield p-neopentylbenzoic acid as a beige solid, mp 191°-193° C. maintaining a temperature of 0°-50° C. over a period of 35 minutes The dark red mixture was stirred at an ambient temperature heated slowly to reflux for 3 hours cooled The mixture was stirred for 1/2 hours two layers were separated The aqueous layer was extracted with methylene chloride the combined organic layers were evaporated to yield a brown oily residue The residue was heated stirred cooled the mixture was extracted with ether stirred for 1 hour The solid was collected by filtration washed with water dissolved in ethyl acetate dried evaporated to yield a solid The solid was crystallized from acetone

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

Procedure: To a solution of neopentylbenzene (9.20 g, 62 mmol) in acetic anhydride (30 mL) cooled in an ice bath was slowly added a solution of nitric acid (3.5 mL, 83 mmol) in acetic anhydride (10 mL). The reaction was allowed to warm to room temperature for 18 hours. The yellow reaction mixture was added to ice water and extracted with diethylether (3×). The organic layers were combined, washed with brine, dried over anhydrous magnesium sulphate, filtered, and concentrated in vacuo. This provided a 1:1 mixture of ortho and para nitro substituted compounds as a yellow solid. To this yellow solid dissolved in methanol (100 mL) was added acetic anhydride (8.4 mL, 89 mmol) and 10% palladium on carbon (700 mg, 7 mmol) and the reaction mixture hydrogenated at a pressure of 40 psi for 3 hours. The reaction was filtered through celite, concentrated in vacuo, and purified by silica gel column chromatography eluting with a 0-50% ethyl acetate/hexanes gradient. This provided the title compound (2.79 g, 22%) as a white solid. extracted with diethylether (3×) washed with brine dried over anhydrous magnesium sulphate filtered concentrated in vacuo This provided a 1:1 mixture of ortho and para nitro substituted compounds as a yellow solid The reaction was filtered through celite concentrated in vacuo purified by silica gel column chromatography eluting with a 0-50% ethyl acetate/hexanes gradient

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

Procedure: A process for the preparation of 2-neopentylanthraquinone, wherein neopentylbenzene is acylated with phthalic anhydride by a Friedel-Crafts reaction to give 2-(4-neopentylbenzoyl)-benzoic acid and the latter is cyclized in the presence of a strong anhydrous acid to give a composition consisting essentially of 2-neopentylanthraquinone without isomerization or degradation of the neopentyl group taking place.

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

Procedure: In the novel process, neopentylbenzene (1) is acylated in a first step with phthalic anhydride (2) under Friedel-Crafts conditions to give 2-(4-neopentylbenzoyl)-benzoic acid (3). ##STR3##