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With sulfuric acid |
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With sulfuric acid for 2.5h; Heating; |
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With sulfuric acid at 100℃; for 2.5h; |
81
l-(4-tert-Butyl-phenyl)-3-chloro-propan-l-one (45.6g, 447 mmol) was taken up in concentrated sulfuric acid (20OmL) and the resulting mixture was heated to 100 0C with stirring for 2.5 hours. TLC indicated that all of the starting material had been consumed. After cooling to RT, the reaction mixture was very carefully poured onto about IKg of crushed ice. Then some diethyl ether was added and the mixture was stirred carefully until it had cooled to about RT. Ethyl acetate (1200 mL) was added and after partitioning, the layers were separated. The acidic layer was then further extracted with ethyl acetate (2X200mL). The combined ethyl acetate layers were washed with saturated sodium bicarbonate (5X300mL). Finally the ethyl acetate layer was dried over magnesium sulfate, filtered, concentrated and pumped to dryness to afford the title compound as a colorless oil (15.764g). |
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With sulfuric acid at 100℃; for 2.5h; |
23 5-tert-Butyl-indan-1-one
Example 23 5-tert-Butyl-indan-1-one 1-(4-tert-Butyl-phenyl)-3-chloro-propan-1-one (45.6 g, 447 mmol) was taken up in concentrated sulfuric acid (200 mL) and the resulting mixture was heated to 100° C. with stirring for 2.5 hours. TLC indicated that all of the starting material had been consumed. After cooling to room temperature, the reaction mixture was very carefully poured onto about 1 Kg of crushed ice. Then some diethyl ether was added and the mixture was stirred carefully until it had cooled to about room temperature. Ethyl acetate (1200 mL) was added and after partitioning, the layers were separated. The acidic layer was then further extracted with ethyl acetate (2*200 mL). The combined ethyl acetate layers were washed with saturated sodium bicarbonate (5*300 mL). Finally the ethyl acetate layer was dried over magnesium sulfate, filtered, concentrated and pumped to dryness to afford the title compound as a colorless oil (15.764 g). |
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With sulfuric acid at 100℃; for 2.5h; |
116; 118 5-tert-Butyl-indan-1-one
1-(4-tert-Butyl-phenyl)-3-chloro-propan-1-one (45.6 g, 447 mmol) was taken up in concentrated sulfuric acid (200 mL) and the resulting mixture was heated to 100° C. with stirring for 2.5 hours. TLC indicated that all of the starting material had been consumed. After cooling to room temperature, the reaction mixture was very carefully poured onto about 1 Kg of crushed ice. Then some diethyl ether was added and the mixture was stirred carefully until it had cooled to about room temperature. Ethyl acetate (1200 mL) was added and after partitioning, the layers were separated. The acidic layer was then further extracted with ethyl acetate (2*200 mL). The combined ethyl acetate layers were washed with saturated sodium bicarbonate (5*300 mL). Finally the ethyl acetate layer was dried over magnesium sulfate, filtered, concentrated and pumped to dryness to afford the title compound as a colorless oil (15.764 g). |
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With sulfuric acid at 95℃; for 2.5h; |
56.E
EXAMPLE 56E 5-tert-butyl-1-indanone; Example 56D (22.25 g, 99 mmol) was dissolved in concentrated sulfuric acid (100 ml) and heated on a water bath at 95° C. for 2.5 hours. The reaction mixture was cooled, poured onto ice, and extracted with diethyl ether. The combined organic extracts were washed with saturated aqueous sodium bicarbonate, dried with magnesium sulfate, and the filtrate was evaporated under reduced pressure to provide the title compound which was used without further purification in the next step. |
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With sulfuric acid In dichloromethane at 90℃; for 2h; |
6.2
Step 2: Sulfuric acid (448 ml, 5 times) was slowly heated to 90°C, a solution of 1 -(4-tert- butylphenyl)-3-chloropropan-1-one (88 g, 390 mmol) in dichloromethane (176 ml, 2 times) was added drop wise for 1 h and stirred the reaction contents for 1 h at the sametemperature. On completion of the reaction, poured the reaction contents into crushed ice (500 g) and the product extracted with ethyl acetate (3 * 300 ml). Combined extract was washed with 5% sodium carbonate (2 * 100 ml) and washed with water (200 ml). Dried the contents over sodium sulfate and concentrated under reduced pressure to obtain the crude product as a pale yellow colored liquid (72 g, crude). |
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With sulfuric acid |
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| 3.7 kg |
With sulfuric acid In dichloromethane at 90℃; for 2h; Large scale; |
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With sulfuric acid at 95℃; for 2.5h; |
1B EXAMPLE 1B 5-tert-butyl-1-indanone
[0192] 1-(4-tert-Butylphenyl)-3-chloro-1-propanone (22.25 g, 99 mmol) was dissolved in concentrated sulfuric acid (100 ml) and heated on a water bath at 95° C. for 2.5 hours. The reaction mixture was cooled, poured onto ice, and extracted with diethyl ether. The combined organic extracts were washed with saturated aqueous sodium bicarbonate, dried with magnesium sulfate, and the filtrate was evaporated under reduced pressure to provide the title compound which was used without further purification in the next step. |
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