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[ CAS No. 531-59-9 ]

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Chemical Structure| 531-59-9
Chemical Structure| 531-59-9
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Product Details of [ 531-59-9 ]

CAS No. :531-59-9 MDL No. :MFCD00006876
Formula : C10H8O3 Boiling Point : 335.3°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :176.17 g/mol Pubchem ID :10748
Synonyms :

Safety of [ 531-59-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 531-59-9 ]

  • Downstream synthetic route of [ 531-59-9 ]

[ 531-59-9 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 93-35-6 ]
  • [ 77-78-1 ]
  • [ 531-59-9 ]
YieldReaction ConditionsOperation in experiment
95% General procedure: 0.4g of SM1 (2.2mmol), SM2 (2.4mmol) and SM3 (2.2mmol), respectively, were dissolved with CH3CN (2.0mL). After that, solid KOH (1.5 or 3 equivalents) was added, and stirred during thirty minutes. 2.1 equivalents of dimethyl sulfate (Me2SO4) were added to the mixture and heating for 48h at 40C. Finally, when reaction was completed (monitored by TLC analysis), the solid was filtered off and dried to afford the corresponding compounds 1 (6,7-dimethoxy-2H-chromen-2-one), 7 (7-methoxy-2H-chromen-2-one) and 13 (7-methoxy-4-methyl-2H-chromen-2-one), respectively.
90.2% With potassium carbonate; potassium iodide; In acetone; at 20℃; for 5h; General procedure: As an example, to a solution of 7-hydroxycoumarin (1.16 g, 7.15 mmol) in acetone (50 mL) was added K2CO3 (2.01 g, 14.55 mmol) and KI (4.38 g, 26.39 mmol) at room temperature. After stirring at room temperature for 10 min, 3-chloropropene (0.90 mL, 11.05 mmol) was added to the reaction mixture, and whole was refluxed at 60 C for 22 h. The solid was separated from the mixture, washed with acetone. Then the mixture was filtered, and the filtrate was washed by acetone (50 mL) three times. Acetone phase was combined, and then evaporated under reduced pressure. The residue was recrystallized in Petroleum ether-ethyl acetate (1:1, V/V) to produce a white needle shaped crystallite (1.31 g). Yield 90.6%.
  • 2
  • [ 93-35-6 ]
  • [ 74-88-4 ]
  • [ 531-59-9 ]
YieldReaction ConditionsOperation in experiment
97% With potassium carbonate; In acetone; at 25℃; for 5h;Inert atmosphere; K2CO3 (2.0 g, 14.5 mmol) and MeI (3.42 g, 24.1 mmol) were added to a solution of 7-hydroxyl coumarin (6) (2.0 g, 12.3 mmol) in acetone (100 mL) and the mixture was reacted for 5 h. After filtration and dilution with EtOAc, the resulting solution was washed with brine and dried over anhydrous Na2SO4. The solvent was removed to afford compound 10 (2.1 g, 97%) as a crystalline solid. 1H NMR (400 MHz, CDCl3) delta 7.95 (d, J = 16.1 Hz, 1H), 7.40 (d, J = 8.7 Hz, 1H), 6.53-6.48 (m, 2H), 6.38 (s, 1H), 3.81 (s, 3H).
73% The 7-hydroxy-coumarin (1g, 6.2mmol) with 30 ml acetone dissolved, adding anhydrous potassium carbonate (1.7g, 12 . 35mmol), stirring the mixture at room temperature for 10 min. Add iodomethane (1.05g, 7 . 41mmol), heating reflux reaction 5h, stop heating, hot filtering, the filtrate is turns on lathe does, ethanol re-crystallization of the white crystal 0.8g, yield 73%.
  • 3
  • [ 531-59-9 ]
  • [ 72167-80-7 ]
YieldReaction ConditionsOperation in experiment
99.5% With N-chloro-succinimide; copper(II) chloride monohydrate; zinc(II) chloride; In acetonitrile; at 82℃; for 0.0833333h; General procedure: To a 50 mL flask, the coumarin (1 mmol), appropriate amount of NXS, the Lewisacid catalyst and 20 mL anhydrous solvent were added in. The mixture was heated toreflux with a condenser under the protection of a drying tube. The reaction progresswas monitored by TLC. When the reaction was completed, the mixture was cooled toroom temperature. The solvent was removed by vacuum rotary evaporation, and theresidue was dispensed in 25 mL 5% sodium hydrogen sulfite (NaHSO3) aqueoussolution and then extracted with 25 mL ethyl acetate (EtOAc) for three times. Theorganic layer was combined, washed with 10 mL water and dried over anhydroussodium sulphate (Na2SO4). After the solvent was removed, the crude product waspurified by silica gel (300-400 mesh) column chromatograph.
80% With N-Bromosuccinimide; In acetonitrile; at 80℃; for 0.0833333h;Microwave irradiation; General procedure: 4-Methyl-6,7-dimethoxycoumarin (0.05 g, 0.227 mmol) was dissolved in acetonitrile (5 ml) in a microwave vessel. N-Bromosuccinimide (0.06 g, 0.340 mmol) was added to the mixture and the vessel inserted into the microwave at 250 W for 5 min at 80 C. The reaction was monitored by thin layer chromatography (silica gel, 3:1 CH2Cl2/EtOAc). Upon completion, the reaction mixture was cooled and the resultant precipitate was collected by vacuum filtration. The crude product was then recrystallized from a mixture of CH2Cl2/MeOH to yield 3-bromo-4-methyl-6,7-dimethoxycoumarin (1a, 0.060 g, 89%)
80% With N-Bromosuccinimide; ammonium acetate; In acetonitrile; at 20℃; for 10h;Inert atmosphere; Under a nitrogen atmosphere, a solution containing <strong>[531-59-9]7-methoxycoumarin</strong> (5.00 g, 28.40 mmol) in acetonitrile (50 mL)N-bromosuccinimide (7.61 g, 42.61 mmol) and ammonium acetate (0.22 g, 2.84 mmol) were added and the mixture was stirred at room temperature for 10 hours. After completion of the reaction, the mixture was extracted with ethyl acetate (3 x 100 mL), saturated brine and water, and the organic layer was washed with anhydrousDried sodium sulfate, evaporated to dryness and separated by silica gel column chromatography (eluent: dichloromethane / petroleum ether, 2: 1,500 ml) to give the white product (5.79 g, 80.0% yield).
56% With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 75℃; for 6h; General procedure: A general procedure for preparation of compounds 5, 9a-b and13: the corresponding N-bromosuccinimide (1.2 equiv) was addedslowly to a solution of <strong>[531-59-9]7-methoxycoumarin</strong> (1 equiv) and sodiumacetate (0.05 equiv) in DMF, and the mixture was stirred at 75 Cfor 6 h. After pouring into brine, and washing, then mixture wasextracted with ethyl acetate. The combined organic layers werewashed with brine, dried over anhydrous Na2SO4 and then filteredand concentrated in vacuum. The product was purified by columnchromatography (0-20% ethyl acetate in petroleum ether).

  • 4
  • [ 531-59-9 ]
  • [ 20921-02-2 ]
YieldReaction ConditionsOperation in experiment
96% palladium-carbon; Preparation of 7-Methoxy-chroman-2-one (Compound 14A) Compound 14A was prepared by hydrogenation of <strong>[531-59-9]7-methoxy-chromen-2-one</strong> catalyzed by 10% Pd/C in 96% yield. MS: 179 (M+1)+.
  • 6
  • [ 150-19-6 ]
  • [ 471-25-0 ]
  • [ 531-59-9 ]
  • [ 51559-36-5 ]
YieldReaction ConditionsOperation in experiment
47%; 11% With trifluoroacetic acid; In chlorobenzene; at 100℃; for 1h;Inert atmosphere; General procedure: A mixture of Phenol derivatives (1) (1.0 mmol), trifluoromethanesulfonic acid (1.0 mmol) and propiolic acid (2a) (0.5 mmol) in PhCl (3.0 mL) was stirred at 100 C for 1 h. After completion of reaction as indicated by TLC, the reaction mixture was poured into H2O, neutralized with NaHCO3 solution and extracted CH2Cl2. The organic layer was washed with 2M NaOH, dried over anhydrous MgSO4. The solvent was removed in vaccum, and the products were purified by silica gel columnchromatography (EtOAc-Hex) to give the desired product 3.
47%; 11% With trifluorormethanesulfonic acid; In chlorobenzene; at 100℃; for 1h; General procedure: Cresol instead of phenol, and the reaction time was 1 hour, the title compound was synthesized in the same manner as in Example 1. White solid (59 mg, 74%)
  • 7
  • 2-formyl-5-methoxyphenyl 2-chloroacetate [ No CAS ]
  • [ 531-59-9 ]
YieldReaction ConditionsOperation in experiment
34% In N,N-dimethyl-formamide;Electrochemical reaction; General procedure: A series of controlled-potential electrolyses ofcompounds 1a-5a at a silver gauze cathode was carried out in DMFcontaining 0.10 M TBABF4. Coulometric n values and yields of thedesired coumarins (1b-5b) are compiled in Table II; each entry correspondsto the average of at least duplicate experiments. Tabulatedn values (the number of electrons transferred per molecule of substrate)were accurate to ±0.10. For all substrates, the coulometricn value was slightly higher than 1, supporting a mechanism wherethe carbon-chlorine bond is mainly cleaved in a one-electron processto give a radical intermediate that cyclizes intramolecularly to forma coumarin.
  • 8
  • [ 673-22-3 ]
  • [ 21204-67-1 ]
  • [ 531-59-9 ]
YieldReaction ConditionsOperation in experiment
71% With N,N-diethylaniline; at 210℃; for 2h; Compound 6 was synthesized following a literature procedure. ADDIN EN.CITE Starevi2011251712517251717tefan StareviBroi, PetraTurk, SamoCesar, JokoRiner, Tea LaninikGobec, StanislavSynthesis and Biological Evaluation of (6- and 7-Phenyl) Coumarin Derivatives as Selective Nonsteroidal Inhibitors of 17beta-Hydroxysteroid Dehydrogenase Type 1Journal of Medicinal ChemistryJournal Of Medicinal ChemistryJ Med ChemJ. Med. Chem.248-6154120111 A mixture of 2-hydroxy-4-methoxybenzaldehyde (1.0 g, 6.58 mmol) and ((methoxycarbonyl)-methylene)triphenylphosphorane (2.75 g, 7.89 mmol) was heated in DMF (65 mL) at 210 C for 2 h. After cooling to room temperature, the reaction mixture was diluted with 5% HCl solution (70 mL) and extracted with ether. The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and then filtered and concentrated in vacuum. The product was purified by column chromatography (0-20% ethyl acetate in petroleum ether). Yield: 822 mg (71%), white solid (mp 111-114 C). 1H NMR (400 MHz, CDCl3) delta 7.60 (d, J = 9.4 Hz, 1H), 7.33 (d, J = 8.6 Hz, 1H), 6.79 (dd, J = 8.6, 2.4 Hz, 1H), 6.73 (d, J = 2.4 Hz, 1H), 6.19 (d, J = 9.5 Hz, 1H), 3.82 (s, 3H). 13C NMR (100 MHz, CDCl3) delta 162.76, 161.16, 155.77, 143.54, 128.83, 112.89, 112.45, 100.75, 55.75.
  • 9
  • [ 17577-28-5 ]
  • [ 531-59-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium hydroxide / ethanol / 1.5 h / 80 °C 2: potassium carbonate; potassium iodide / acetone / 5 h / 20 °C
  • 10
  • [ 531-59-9 ]
  • [ 1417997-93-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 6 h / Inert atmosphere 2: pyridine / dichloromethane / 2 h / 20 °C 3: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / N,N-dimethyl-formamide / 12 h / 90 °C 4: lithium hydroxide / methanol 5: triethylamine / tetrahydrofuran / 1 h / 20 °C 6: hydroxylamine hydrochloride; potassium hydroxide / methanol / 3 h / 20 °C
  • 11
  • [ 531-59-9 ]
  • [ 1809-20-7 ]
  • [ 1499139-80-8 ]
YieldReaction ConditionsOperation in experiment
72% With C17H17Br2N3OPd; silver nitrate; In acetonitrile; at 80℃; for 10h;Schlenk technique; Inert atmosphere; General procedure: In a typical reaction, a Schlenk tube charged with coumarins (0.5mmol), dialkyl phosphite (1.0mmol), NHC palladium complex, AgNO3 and solvent (2mL) was heated at 80C for 10h. The mixture was then cooled, filtered and the filtrate was evaporated. Purification of the residue by column chromatography (silica, petroleum ether/ethylacetate=2/1-1/4, v/v) produced the pure products, which were characterized by 1H NMR and 13C NMR. The analytical data of the products were shown in the Supporting Information.
64% With magnesium(II) nitrate hexahydrate; silver nitrate; In acetonitrile; at 100℃; for 6h;Inert atmosphere; General procedure: In a Schlenk tube, coumarin 1 (0.5mmol), dialkyl H-phosphite 2 (1.0mmol), AgNO3 (0.025mmol, 4.2mg) and Mg(NO3)2·6H2O (0.25mmol, 64mg) were added and charged with Nitrogen (3 cycles). Anhydrous CH3CN (1mL) was then added. After heating in the oil bath at 100C for 6h (monitored by TLC), 5mL ethylacetate was added to dilute the reaction solution. The solution was filtrated, and the solvent was distilled under vacuum. The crude product was purified by silica gel column chromatography to give the desired product 3 using ethylacetate/petroleum ether (1:5 to 2:1) as eluant.
64% With sodium nitrate; silver nitrate; In methanol; at 90℃; for 5h; <strong>[531-59-9]7-Methoxycoumarin</strong> (1.0 mmol, 176 mg) and diisopropyl phosphite (2.0 mmol, 232 mg) were added to a 25 mL reaction flask and dissolved in 5.0 mL of methanol,Then AgNO3 (0.05 mmol, 8.4 mg) and NaNO3 (0.5 mmol, 42.5 mg) were added.The reaction was carried out by heating under stirring in an oil bath,The reaction temperature was 90 C.By TLC tracking the reaction process,Reaction time is 5h,After the reaction,The solvent was distilled off under reduced pressure,To the raffinate was added 10 mL of ethyl acetate,Washed twice with 20 mL of saturated NaHCO3,And then washed with 10 mL of saturated brine once,The solution was concentrated and purified by silica gel column chromatography (eluent: ethyl acetate / petroleum ether = 1/3)To give 0.216 g of a white solid,Yield 64.0%.
  • 12
  • [ 531-59-9 ]
  • [ 2926-29-6 ]
  • [ 1562426-78-1 ]
YieldReaction ConditionsOperation in experiment
67% With dipotassium hydrogenphosphate; In acetone; at 20℃; for 12h;Inert atmosphere; Irradiation; Green chemistry; General procedure: To a tube were added 1a (1.0 equiv), CF 3 SO 2 Na(4.0 equiv),K 2 HPO 4 , Acetone (2 mL). Then the tube was evacuated and backlledwith argon for three times. The tube around condensate water wasstirred at room temperature in argon with the irradiation of Xenon lampfor 12 h. After the reaction was nished, the mixture was washed withsaturated sodium chloride solution and then extracted with ethylacetate for three times. The combined organic layers were dried overNa 2 SO 4 and concentrated under reduced pressure, then puried bychromatography on silica gel.
  • 13
  • [ 531-59-9 ]
  • 2-oxo-2-o-tolylacetic acid [ No CAS ]
  • 7-methoxy-3,4-bis-(2-methylbenzoyl)chromen-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With dipotassium peroxodisulfate; silver nitrate; In water; dimethyl sulfoxide; at 20℃; for 24h;Inert atmosphere; Schlenk technique; Sealed tube; General procedure: A 10mL oven-dried Schlenk-tube was charged with AgNO3 (3.4mg, 10mol%), coumarin (1, 0.2mmol, 1.0equiv), and K2S2O8 (108mg, 0.4mmol, 2.0equiv). The tube was evacuated and backfilled with nitrogen (three times). alpha-Oxocarboxylic acids (2, 0.48mmol, 2.4equiv) in DMSO/H2O (1:1) 2mL were added by syringe. The tube was then sealed and the mixture was stirred for 24h at room temperature. Upon completion of the reaction, the mixture was diluted with EtOAc, filtered through a pad of Celite, and the filtrate was then removed under vacuo. The residue was purified with chromatography column on silica gel (gradient eluent of EtOAc/petroleum ether: 1:30 to 1:15) to give the corresponding products 3 or 4 in yields listed in Tables 2 and 3.
  • 14
  • [ 616-47-7 ]
  • [ 93-35-6 ]
  • [ 531-59-9 ]
YieldReaction ConditionsOperation in experiment
70% With Di-tert-butyl acetylenedicarboxylate; In neat (no solvent); at 100℃; for 0.0833333h;Microwave irradiation; Green chemistry; General procedure: In a 10-mL reaction vial, a mixture of N-methylimidazole (3, 0.26 g, 2.0 mmol) and dimethyl acetylenedicarboxylate (2a, 0.24 mL, 2.0 mmol) under solvent-free condition was stirred for 1 min. Subsequently, 4-hydroxycoumarin (1a, 0.32 g, 2.0 mmol) was added to the reaction mixture, and the reaction vial was capped and pre-stirred for 20 s. The mixture was subjected to microwave irradiation at a power of 600 W for 6 min at 100 C. Upon completion, monitored by TLC, the reaction mixture was cooled to room temperature. The resulting precipitate was separated by filtration and recrystallized from diethyl ether (Et2O) to afford the pure compound 4a.
  • 15
  • [ 93-35-6 ]
  • [ 762-42-5 ]
  • [ 531-59-9 ]
YieldReaction ConditionsOperation in experiment
98% With 1-methyl-1H-imidazole; In neat (no solvent); at 100℃; for 0.0666667h;Microwave irradiation; Green chemistry; General procedure: In a 10-mL reaction vial, a mixture of N-methylimidazole (3, 0.26 g, 2.0 mmol) and dimethyl acetylenedicarboxylate (2a, 0.24 mL, 2.0 mmol) under solvent-free condition was stirred for 1 min. Subsequently, 4-hydroxycoumarin (1a, 0.32 g, 2.0 mmol) was added to the reaction mixture, and the reaction vial was capped and pre-stirred for 20 s. The mixture was subjected to microwave irradiation at a power of 600 W for 6 min at 100 C. Upon completion, monitored by TLC, the reaction mixture was cooled to room temperature. The resulting precipitate was separated by filtration and recrystallized from diethyl ether (Et2O) to afford the pure compound 4a.
  • 16
  • [ 109-99-9 ]
  • [ 531-59-9 ]
  • 7-methoxy-3-(tetrahydrofuran-2-yl)-2H-chromen-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With di-tert-butyl peroxide; copper diacetate; potassium iodide; In tetrahydrofuran; at 100℃; for 24h;Inert atmosphere; General procedure: 0.6 mmol DTBP in 1.5 mL THF was added into the 10 mL flask charged with 0.2 mmol coumarin, 10 mol % Cu(OAc)2, 20 mol % KI. The reaction mixture was stirred at 100 C for specified hours, then cooled down to room temperature. Filtrate was concentrated under reduced pressure. The residue was purified by chromatography on silica gel (elute: EtOAc/Petroleum ether 1/3-1/10, v/v) to give the desired product.
  • 17
  • [ 646-06-0 ]
  • [ 531-59-9 ]
  • 3-(1,3-dioxolan-2-yl)-7-methoxy-2H-chromen-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With di-tert-butyl peroxide; copper diacetate; potassium iodide; In tetrahydrofuran; at 100℃; for 24h;Inert atmosphere; General procedure: 0.6 mmol DTBP in 1.5 mL THF was added into the 10 mL flask charged with 0.2 mmol coumarin, 10 mol % Cu(OAc)2, 20 mol % KI. The reaction mixture was stirred at 100 C for specified hours, then cooled down to room temperature. Filtrate was concentrated under reduced pressure. The residue was purified by chromatography on silica gel (elute: EtOAc/Petroleum ether 1/3-1/10, v/v) to give the desired product.
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