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CAS No. : | 2879-20-1 | MDL No. : | MFCD00006823 |
Formula : | C10H10O3 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | HGVWMTAIIYNQSI-UHFFFAOYSA-N |
M.W : | 178.18 | Pubchem ID : | 76143 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
65% | With sodium hydroxide; In ethanol; dichloromethane; water; at 20℃; | The 534mg (3mmol) 6- acetyl-1,4-benzo-dioxane, 160mg (4mmol) of sodium hydroxide in 100mL single-neck flask, add 10 drops of water, 20mL ethanol and dissolved; the 813mg (3mmol) 4- (9- (9H-Carbazol-yl)) benzaldehyde was dissolved in 10mL of dichloromethane, ethanol and added dropwise to the mixture, stirred at room temperature overnight, filtered, ethanol, washed with petroleum ether, and dried to give a pale yellow solid (LJZ-5-32) 842mg the yield was 65%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With sodium hydride; In dimethyl sulfoxide; mineral oil; Petroleum ether; at 15 - 20℃; for 24h;Inert atmosphere; | The title compound was prepared according to the published protocol1. A 60 % suspension of sodium hydride in mineral oil (0.2 g, 5.0 mmol) was washed with petroleum benzin (20 ml) twice, anhydrous DMSO (4 ml) was added. After being stirred for 30 mm at room temperature under argon, the flask was cooled down to 15 00 and a solution of methyl3-chlorobenzoate (0.853 g, 5.0 mmol) and 1 -(2,3-dihydro-1 ,4-benzodioxin-6-yl)ethanone (0.712 g, 4.0 mmol) in DMSO (4 ml) was added dropwise. Upon completion of addition, the reaction mixture was stirred 24 h at room temperature, then poured slowly into crushed ice (50 g) containing 85 % phosphoric acid (1 ml). The resulting precipitate was collected by filtration, washed with water (50 ml) and air dried. The resulting crude product wasrecrystallized from methanol to provide sery595 (590 mg, 47 %) as a light-yellow powder.TLC (hexane:EtOAc, 3/1 v/v): RE = 0.53.1H NMR (400 MHz, DMSO-d6) 6 = 8.24 (t, J = 1.8 Hz, 1H), 8.10 (d, J = 7.8 Hz, 1H), 7.79-7.73(m, 2H), 7.69 (m, 1H), 7.58 (t, J 7.8 Hz, 1H), 7.32 (s, 1H), 7.02 (d, J = 8.3 Hz, 1H), 4.39-4.29 (m, 4H), (in 1H NMR spectrum 6.5% of diketone form is present).130 NMR (100.6 MHz, DMSO-d6) 6 = 186.2, 181.6, 148.1, 143.5, 136.6, 133.8, 132.4, 130.7,127.8, 126.9, 125.8, 121.7, 117.4, 116.7, 93.1, 64.6, 63.9.LC MS (RP18-100A, gradient 0% CH3CN/100% H20 - 100% CH3CN in 50 mm), RT 45.8 mm and mass 317.04 (100%), 318.99 (35%) ([M+H]).M.p. 106-1 07 C. |
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