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CAS No. : | 3010-81-9 | MDL No. : | MFCD00014898 |
Formula : | C22H22O4 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | JCLOLVVCZNYDIP-UHFFFAOYSA-N |
M.W : | 350.41 | Pubchem ID : | 76380 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
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* 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 |
---|---|---|
94% | General procedure: Sodium borohydride (8.0 mg, 95%, 0.20 mmol) was added to a solution of aryl alcohol (1a-i, 0.20 mmol) in MeCN (2.0 mL) under an argon atmosphere at 0 C. The mixture was stirred at 0 C for 15 min. Trimethylsilyl chloride (52 μL, 98%, 0.40 mmol) and potassium iodide (33.2 mg, 99%, 0.20 mmol) were added to the mixture at 0 C. The reaction mixture was stirred at room temperature (rt) under an argon atmosphere until no further TLC changes were observed. After the mixture was diluted with EtOAc (5 mL), the reaction was quenched by the addition of a saturated aqueous NaHCO3 solution (2 mL) and Na2S2O3 solution (2 mL). The layers were separated. The aqueous layer was extracted with EtOAc (5 mL). The combined organic layer was washed with water, brine, dried over anhydrous Na2SO4, and concentrated. The residue was purified by silica gel chromatography to give the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With acetyl chloride; In toluene; at 100℃; for 2h;Inert atmosphere; | General procedure: AcCl (3 equiv) was added to the appropriate alcohol (1 equiv) dissolved in toluene (2mL/mmol) and the mixture was heated to 100C. After 2h, the volatiles were removed under reduced pressure and the solid was dissolved in dry toluene (4mL/mmol) and evaporated to dryness three times. The crude product was used without any further purification. |
With acetyl chloride; In toluene; for 1h;Reflux; | Tetrakis(4-methoxyphenyl)methane 1 Acetyl chloride (excess, 5.0 mL) was added to a solution of <strong>[3010-81-9]tris(4-methoxyphenyl)methanol</strong> 2 (1.0 equiv, 4.9 mmol, 1.7 g) in toluene (30 mL). After heating at reflux for 1 h, the toluene was removed under reduced pressure. The product was precipitated by addition of light petroleum, collected by filtration and dried under vacuum. Compound 3 was obtained as an orange solid, and used without further purification. To a solution of 4-bromoanisole (1.1 equiv, 2.1 mmol, 390 mg) in dry THF (20 mL) at RT under a nitrogen atmosphere was added magnesium turnings (1.1 equiv, 2.1 mmol, 51 mg), and the solution was stirred at reflux for 1 h. This solution was added to a solution of trityl chloride 3 (1.0 equiv, 1.9 mmol, 700 mg) in dry THF at RT. After heating at reflux for 1 h, water (20 mL) was added at RT. Most of the THF was removed under reduced pressure, then the aqueous phase was extracted with CH2Cl2 (3 * 20 mL). The combined organic phases were dried over MgSO4, filtered, and then concentrated under reduced pressure. Silica gel flash column chromatography (eluent: CH2Cl2) of the residue gave compound 1 as a white solid (225 mg, 0.5 mmol, 27% yield). The NMR analysis is similar to the one in the literature. 9 1H NMR (300.13 MHz, CDCl3, 25 C): δ = 7.07 (d, 3JH-H 9.0 Hz, 8H, aromatic CH), 6.77 (d, 3JH-H 9.0 Hz, 8H, aromatic CH), 3.78 (s, 12H, CH3). Mp 250-252 C (Lit.<ce-sup primary_key="ce-sup-35847677-none">9,10 246-248 C). | |
With thionyl chloride; In toluene; at 0℃; for 4.5h;Reflux; | To <strong>[3010-81-9]tris(4-methoxyphenyl)methanol</strong> (7.50 g, 21.4 mmol) in toluene (15 ml) at 0 C thionyl chloride (2.95 ml, 40.7 mmol) was added, followed by refluxing for 4.5 h. After cooling to rt n-heptane (40 ml) was added and the resulting precipitate was filtered off under N2 and washed with n-heptane (30 ml). The residue was twice recrystallized from n-heptane/toluene to result in 6.0 g ofy ellow crystals. 526 mg thereof were added to a mixture of ethylene glycol (194 mg, 3.13 mmol) and pyridine (2.2 ml). After stirring at rt for 25 h phosphate buffer (pH 7, 50 ml) was added, followed by extraction with Et2O. The combined organic layerswere dried (MgSO4) and concentrated in vacuo. Purification was accomplished by CC (EtOAc/n-pentane 35:65 1% EtMe2N).Yield: 235 mg (32%) of 8f and 37 mg (5%) of 12; 8f: colorless oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.6 g | General procedure: The appropriate Grignard reagent (1.3 equiv) generated according to GP 1 was added to ketone 15 (1.0 equiv) suspended in THF (2mL/mmol) and heated to 60C for 2h. At 25C the mixture was quenched with saturated aqueous NH4Cl solution and extracted with Et2O. The organic phases were dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by recrystallization or by column chromatography over silica gel. |
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