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CAS No. : | 3016-97-5 | MDL No. : | MFCD00014087 |
Formula : | C20H14O2 | Boiling Point : | - |
Linear Structure Formula : | C6H5COC6H4COC6H5 | InChI Key : | NPENBPVOAXERED-UHFFFAOYSA-N |
M.W : | 286.32 | Pubchem ID : | 76395 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H317-H319 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | With aluminum (III) chloride; In dichloromethane; at 20℃; for 12h;Inert atmosphere; | Aluminum trichloride (1.37 g, 10.33 mmol) was added to a solution of terephthaloyl dichloride (1.0 g, 4.42 mmol) in anhydrous dichloromethane and excess benzene. After stirring for 12 h at room temperature under an inert atmosphere of nitrogen gas, the reaction mixture treated with 10% HCI (50 mL) and the products were extracted with ethyl acetate (3 * 20 mL). The combined organic phases were washed with brine and dried over sodium sulfate. After the organic layer was concentrated under reduced pressure, purification using flash chromatography (silica gel, hexanes: ethyl acetate, 80:20) afforded 1 ,4-dibenzoyl benzene 1 (0.405 g, 1.41 mmol) in a 32% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With potassium fluoride; potassium phosphate; copper; Trimethylacetic acid; at 100℃; under 760.051 Torr; for 24h; | General procedure: A 25 mL reaction flask was charged with copper nanoparticles (0.1 mmol)Aryl diiodonium (0.5 mmol),Benzene boronic acid (1.5 mmol),Potassium phosphate (1.0 mmol),Potassium fluoride (0.5 mmol), pivalic acid (0.5 mmol) and polyethylene glycol-400 (2.0 g)And the introduction of an atmospheric carbon monoxide.The reaction mixture was reacted at 100 C until the reaction was complete and cooled to room temperature,The product was isolated by column chromatography after evaporation of the solvent under reduced pressure. |
EXAMPLE 3 A reaction flask was purged with nitrogen and charged with 58.5 grams of aluminum trichloride and 160 milliliters of benzene. A mixture of 40.6 grams of terephthaloyl chloride in 280 milliliters of benzene was added to the reaction flask from a dropping funnel over a period of 50 minutes. The temperature of the reaction mixture was maintained at about 44-47 C. for a period of about 40 minutes and raised to 68 C. for about one and one-half hours. The reaction vessel and contents were cooled with ice water bath and ice water mixed with the reaction mixture. Methylene chloride was added and the aqueous and organic layers separated. The organic layer was washed three times with aqueous sodium bicarbonate and washed twice with water. The organic layer was dried over anhydrous sodium sulfate. The particulate sodium sulfate separated and the organic solvents removed by evaporation. The resultant crude product remaining after the evaporation was recrystallized from absolute alcohol containing about 0.5 percent benzene. Thirty grams of 1,4-dibenzoylbenzene were obtained which had a melting range of 155-160 C. | ||
Step 1: 1,4-Dibenzoylbenzene is prepared essentially as described by Noelting and Kohn, Ber. 19, 147 (1886). Terephthaloyl dichloride (20.3 g, 0.1 mole) is dissolved in benzene (350 ml) and anhydrous aluminum chloride (30 g, 0.22 mole) is added. The mixture is heated at 70 for 7 hours, cooled to 20 and maintained at this temperature for 18 hours with continual stirring. The reaction mixture is then added to 1 l crushed ice and 20 ml 37% hydrochloric acid. The benzene solution is washed three times with water and twice with sodium bicarbonate solution. The excess benzene is removed by distillation. The resulting crystalline material is recrystallized from dimethylformamide, yield 22 g (76% of theory) white crystals mp 158-9. |
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