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CAS No. : | 6342-80-9 | MDL No. : | MFCD00463187 |
Formula : | C11H12O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XQODIRIVQXQUFN-UHFFFAOYSA-N |
M.W : | 192.21 | Pubchem ID : | 240446 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | 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 |
---|---|---|
44% | With Eaton?s reagent; at 20℃; for 72h; | Carboxylic acid 9 (4.99 g, 23.7 mmol) was mixed with Eaton's reagent (47.5 mL, 3 g per mmol of carboxylic acid 9) and stirred for 72 h at room temperature. The mixture was then poured over ice, neutralized, and extracted with EtOAc (3×75 mL). The organic layer was dried over sodium sulfate, concentrated and purified by flash chromatography using a prepacked 100 g silica column [solvent A: EtOAc; solvent B: hexane; gradient: 7% A/93% B (1 CV), 7% A/93% B?60% A/40% B (10 CV), 60% A/40% B (2 CV); flow rate: 40 mL/min; monitored at 254 nm and 280 nm] to afford ketone 11 (2.01 g, 10.5 mmol, 44%) as a yellow solid. 1H NMR (CDCl3, 600 MHz) delta 7.06 (1H, d, J=8.4 Hz), 6.62 (1H, d, J=8.4 Hz), 3.61 (3H, s), 3.57 (3H, s), 2.70 (2H, t, J=5.4 Hz), 2.25 (2H, t, J=5.4 Hz). 13C NMR (CDCl3, 150 MHz) delta 204.6, 157.1, 147.4, 145.0, 130.7, 119.4, 112.0, 59.8, 55.8, 36.0, 22.1. |
With PPA; | EXAMPLE 2 4,5-Dimethoxy-1-indanone A reaction mixture of 14.3 g. of 3-(2,3-dimethoxyphenyl)propionic acid and 128 g. of polyphosphoric acid, was stirred with a glass rod at 85-87 C. for 10 minutes. The reaction mixture was poured onto approximately 500 g. of ice and stirred for thirty minutes. The mixture was then filtered and the residue was washed with approximately equal volume portions of water, a saturated aqueous sodium hydroxide solution and then water. The residue was dried in vacuo, to yield 8.1 g. of 4,5-dimethoxy-1-indanone as a brown solid. M.P. 73-74 C. | |
In methanesulfonic acid; | b) 2,3-Dihydro-4,5-dimethoxy-1H-inden-1-one Under nitrogen a solution of 3-(2,3-dimethoxyphenyl)-propanoic acid (2 g) in 50 ml methanesulfonic acid was warmed at 60 0C and kept there for 2 hours. The reaction mixture was cooled to room temperature and poured into ice/water. After extraction with ethyl acetate the organic layer was washed with a 1N aqueous sodium hydroxyde solution, dried over magnesium sulfate, filtered and evaporated in vacuo yielding 1.2g of 2,3-dihydro-4,5-dimethoxy-1H-inden-1-one, M.S. (C.I.) (M/Z): 193 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With trimethylammonium heptachlorodialuminate; In dichloromethane; at 80℃; for 1h;Microwave irradiation; | Ketone 11 (0.70 g, 3.2 mmol) was added to a 20 mL microwave vial with [TMAH] [Al2Cl7] (10.0 mL, 7.26 mmol) and microwaved for 1 h at 80 C. The mixture was poured into water, extracted with CH2Cl2 (3×30 mL), dried over sodium sulfate and purified by flash chromatography using a prepacked 50 g silica column [solvent A: EtOAc; solvent B: hexane; gradient: 12% A/88% B (1 CV), 12% A/88% B?100% A/0% B (10 CV), 100% A/0% B (2 CV); flow rate: 50 mL/min; monitored at 254 nm and 280 nm] to afford phenol 15 (0.42 g, 2.36 mmol, 72%) as a brown solid. 1H NMR (CDCl3, 600 MHz) delta 7.35 (1H, d, J=10.2 Hz), 6.92 (1H, d, J=10.2 Hz), 5.81 (1H, s), 3.97 (3H, s), 3.07 (2H, t, J=6.6 Hz), 2.69 (2H, t, J=6.6 Hz). 13C NMR (CDCl3, 150 MHz) delta 206.0, 150.9, 142.1, 140.5, 131.4, 116.1, 110.4, 56.4, 36.5, 21.9. |
aluminium trichloride; In 1,2-dichloro-ethane; | c) 2,3-Dihydro-4-hydroxy-5-methoxy-1H-inden-1-one Under a nitrogen atmosphere <strong>[6342-80-9]2,3-dihydro-4,5-dimethoxy-1H-inden-1-one</strong> (31.7 g) was dissolved in 600 ml of anhydrous 1,2-dichloroethane and cooled to 0 0C. Aluminum chloride (44 g) was added in portions and the reaction mixture was heated to 60 0C for 17 hours, cooled to room temperature and poured into ice/water. After extraction with dichloromethane the organic layer was dried and evaporated. The residue was crystallized from ethyl acetate to give 20.5 g of 2,3-dihydro-4-hydroxy-5-methoxy-1H-inden-1-one, M.S. (C.I.) (M/Z): 179 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | zinc(II) iodide; In toluene; acetonitrile; at 50℃; for 16h; | Under nitrogen, zinc iodide (1.5 g, 4.68 mmol), trimethylsilyl cyanide (27.1 ml_, 203.0 mmol) were added sequentially to the solution of <strong>[6342-80-9]4,5-dimethoxy-1-indanone</strong> (30.0 g, 156.1 mmol) in toluene (100 ml_) and acetonitrile (24 mL). The reaction mixture was heated to 5O0C for 16 h. The reaction mixture was cooled to room temperature and diluted with 100 mL of toluene and 60 mL of a saturated aqueous sodium bicarbonate solution. After the mixture was stirred for 1 h, the layers were separated. The organic layer was washed by brine (60 mL) and dried (Na2SO4). The organic layer was concentrated in vacuo and the residue was purified by chromatography (EtOAc / Hexanes: 5/95) to afford 1-trimethylsilanyloxy-4,5- dimethoxyindane-1-carbonitrile (33.1 g, 73%). |
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