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[ CAS No. 4282-24-0 ]

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Chemical Structure| 4282-24-0
Chemical Structure| 4282-24-0
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Product Details of [ 4282-24-0 ]

CAS No. :4282-24-0 MDL No. :MFCD01860231
Formula : C6H4O5 Boiling Point : 375.2°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :156.09 g/mol Pubchem ID :-
Synonyms :

Safety of [ 4282-24-0 ]

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 [ 4282-24-0 ]

* 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.

  • Downstream synthetic route of [ 4282-24-0 ]

[ 4282-24-0 ] Synthesis Path-Downstream   1~31

  • 3
  • [ 4282-24-0 ]
  • [ 488-93-7 ]
YieldReaction ConditionsOperation in experiment
at 250℃;
  • 4
  • [ 104721-77-9 ]
  • [ 4282-24-0 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride
With sodium hydroxide
  • 5
  • [ 101306-25-6 ]
  • [ 4282-24-0 ]
YieldReaction ConditionsOperation in experiment
97% With tetrabutyl ammonium fluoride In tetrahydrofuran at 67℃; for 12h;
YieldReaction ConditionsOperation in experiment
Prangol , H2O2, wss. NaOH;
.............., 1. wss. NaOH, 3percentig. H2O2, RT, 2. 80grad;
YieldReaction ConditionsOperation in experiment
With water; silver(l) oxide
YieldReaction ConditionsOperation in experiment
With water; silver(l) oxide Behandeln des Reaktionsprodukts mit Zinkstaub und Ammoniumchlorid-Loesung;
With hydroxylamine hydrochloride; sodium acetate Erhitzen des entstandenen Oxims mit Acetanhydrid auf 150grad; Kochen des Nitrils mit Natronlauge und nachfolgendes Entbromen mit Zinkstaub und Ammoniumchlorid-Loesung;
YieldReaction ConditionsOperation in experiment
With water; silver(l) oxide Behandeln des Reaktionsprodukts mit Zinkstaub und Ammoniumchlorid-Loesung;
With hydroxylamine hydrochloride; sodium acetate Erhitzen des entstandenen Oxims mit Acetanhydrid auf 150grad; Kochen des Nitrils mit Natronlauge und nachfolgendes Entbromen mit Zinkstaub und Ammoniumchlorid-Loesung;
YieldReaction ConditionsOperation in experiment
With potassium hydroxide anschliessend Erhitzen mit Hydroxylamin-hydrochlorid und wss. Salzsaeure und Erhitzen des Reaktionsprodukts mit Acetanhydrid und anschliessend mit wss. Kalilauge;
YieldReaction ConditionsOperation in experiment
With dihydrogen peroxide
  • 12
  • [ 124-38-9 ]
  • [ 4282-24-0 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-Furoic acid With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 1.5h; Stage #2: carbon dioxide In tetrahydrofuran; hexanes at -78 - -10℃; for 1h; Stage #3: With hydrogenchloride In tetrahydrofuran; hexanes; water at -10℃; 9.1 n-Butyllithium (2.5M in hexanes, 196 mL, 491 mmol) was introduced into a dry 3 L 3- necked flask fitted with an addition funnel, argon inlet, and mechanical stirrer. The mixture was diluted with dry THF (500 mL), and cooled to -78 0C. 3-furoic acid (25 g, 223 mmol) was added as solution in THF (500 mL) dropwise. The mixture was stirred for 1.5 h, at which point dry carbon dioxide was bubbled through the reaction mixture for 1 h. After warming gradually to -10 0C, the resultant thick white slurry was treated with aqueous HCl (2 N, 446 mL). The two layers were separated, and the aqueous layer was extracted with EtOAc (3 x 300 mL). The combined organics were dried (Na2SO4), filtered, and concentrated to afford crude furan-2,3-dicarboxylic acid as an orange solid (44 g) which was used without further purification. 1H NMR (300 MHz, 6-acetone) δ 7.06 (d, 7= 1.7, l), 7.97 (d, J= 1.7, 1), 10.7 (bs, 2H);TLC (CHClj/MeOH/H2O 6:4:1) Rf = 0.56.
  • 13
  • [ 88-14-2 ]
  • [ 4282-24-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1.) LDA / 1.) THF, -78 deg C, 0.5 h, 2.) -78 deg C to 25 deg C, 2 h 2: 1.) n-BuLi / 1.) THF, -78 deg C, 0.5 h, 2.) ether, -78 deg C to 25 deg C, 2 h 3: 97 percent / (nBu)4N(1+)*F(1-) / tetrahydrofuran / 12 h / 67 °C
  • 14
  • [ 18292-14-3 ]
  • [ 4282-24-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) n-BuLi / 1.) THF, -78 deg C, 0.5 h, 2.) ether, -78 deg C to 25 deg C, 2 h 2: 97 percent / (nBu)4N(1+)*F(1-) / tetrahydrofuran / 12 h / 67 °C
  • 15
  • [ 855461-96-0 ]
  • [ 4282-24-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: concentrated sulfuric acid 2: aq. NaOH solution
  • 16
  • [ 488-93-7 ]
  • [ 124-38-9 ]
  • [ 4282-24-0 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-Furoic acid With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 1.5h; Stage #2: carbon dioxide In tetrahydrofuran; hexanes for 1h; Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexanes at -10℃; 9.1 n-Butyllithium (2.5M in hexanes, 196 mL, 491 mmol) was introduced into a dry 3 L 3-necked flask fitted with an addition funnel, argon inlet, and mechanical stirrer. The mixture was diluted with dry THF (500 mL), and cooled to -78 °C. 3-furoic acid (25 g, 223 mmol) was added as solution in THF (500 mL) dropwise. The mixture was stirred for 1.5 h, at which point dry carbon dioxide was bubbled through the reaction mixture for 1 h. After warming gradually to -10 °C, the resultant thick white slurry was treated with aqueous HCl (2 N, 446 mL). The two layers were separated, and the aqueous layer was extracted with EtOAc (3 x 300 mL). The combined organics were dried (Na2SO4), filtered, and concentrated to afford crude furan-2,3-dicarboxylic acid as an orange solid (44 g) which was used without further purification. 1H NMR (300 MHz, d6-acetone) δ 7.06 (d, J = 1.7, 1), 7.97 (d, J = 1.7, 1), 10.7 (bs, 2H);TLC (CHCl3/MeOH/H2O 6:4:1) Rf = 0.56.
Stage #1: 3-Furoic acid; carbon dioxide With n-butyllithium In tetrahydrofuran; hexanes at -78 - -10℃; for 2.5h; Stage #2: With hydrogenchloride In tetrahydrofuran; hexanes; water 9.1 Step 1 n-Butyllithium (2.5M in hexanes, 196 mL, 491 mmol) was introduced into a dry 3 L 3-necked flask fitted with an addition funnel, argon inlet, and mechanical stirrer. The mixture was diluted with dry THF (500 mL), and cooled to -78° C. 3-furoic acid (25 g, 223 mmol) was added as solution in THF (500 mL) dropwise. The mixture was stirred for 1.5 h, at which point dry carbon dioxide was bubbled through the reaction mixture for 1 h. After warming gradually to -10° C., the resultant thick white slurry was treated with aqueous HCl (2 N, 446 mL). The two layers were separated, and the aqueous layer was extracted with EtOAc (3×300 mL). The combined organics were dried (Na2SO4), filtered, and concentrated to afford crude furan-2,3-dicarboxylic acid as an orange solid (44 g) which was used without further purification. 1H NMR (300 MHz, d6-acetone) δ7.06 (d, J=1.7, 1), 7.97 (d, J=1.7, 1), 10.7 (bs, 2H);TLC (CHCl3/MeOH/H2O 6:4:1) Rf=0.56.
  • 17
  • [ 67-56-1 ]
  • [ 4282-24-0 ]
  • [ 52900-79-5 ]
YieldReaction ConditionsOperation in experiment
93% With chloro-trimethyl-silane at 20℃; for 15.5h; 9.2 A dry 500 mL round bottomed flask was equipped with a stir bar and an argon inlet. The flask was charged with the crude diacid prepared in Step 1 (44 g) dissolved in MeOH (250 mL). To the reaction mixture was added chlorotrimethylsilane (80 mL, 630 mmol) portionwise. After stirring at room temperature for 15.5 h, the solution was concentrated to an oil and silica (5 g) was added. The mixture was suspended in MeOH (100 mL), and the volatiles were removed. Suspension in MeOH (100 mL) and the removal of the volatiles was repeated an additional two times. The residue was applied directly to the top of a flash chromatography column and was eluted hexanes/EtOAc 60:40 to yield dimethyl furan-2,3-dicarboxylate as an orange oil (38 g, 93 % for Step 1 and Step 2 combined). 1H NMR (300 MHz, CDCl3) δ 3.81 (s, 3), 3.86 (s, 3), 6.71 (d, J = 2.8, 1), 7.46 (d, J = 2.8, 1); TLC (hexanes/EtOAc 60:40) Rf = 0.46.
55% With thionyl chloride at 20℃; for 16h; Inert atmosphere;
55% With thionyl chloride at 20℃; for 16h; Furan-2,3-dicarboxylic acid (1 g, 6.41 mmol) is dissolved in MeOH (10 niL). To this solution is added thionyl chloride (1.4 niL, 19.22 mmol). The reaction is allowed to continue stirring at room temperature for 16 h. Add H2O (1 mL) to quench the reaction and remove the MeOH in vacuo. Add additional H2O and extract with EtOAc. Combined organic layers are washed with brine and concentrated in vacuo to yield the title compound without further purification (650 mg, 55%).
With chloro-trimethyl-silane at 20℃; for 15.5h; 9.2 A dry 500 mL round bottomed flask was equipped with a stir bar and an argon inlet. The flask was charged with the crude diacid prepared in Step 1 (44 g) dissolved in MeOH (250 mL). To the reaction mixture was added chlorotrimethylsilane (80 mL, 630 mmol) portionwise. After stirring at room temperature for 15.5 h, the solution was concentrated to an oil and silica (5 g) was added. The mixture was suspended in MeOH (100 mL), and the volatiles were removed. Suspension in MeOH (100 mL) and the removal of the volatiles was repeated an additional two times. The residue was applied directly to the top of a flash chromatography column and was eluted hexanes/EtOAc 60:40 to yield dimethyl furan-2,3-dicarboxylate as an orange oil (38 g, 93 % for Step 1 and Step 2 combined). 1H NMR (300 MHz, CDCl3) δ 3.81 (s, 3), 3.86 (s, 3), 6.71 (d, J = 2.8, 1), 7.46 (d, J = 2.8, 1); TLC (hexanes/EtOAc 60:40) Rf= 0.46.
With chloro-trimethyl-silane at 20℃; for 15.5h; 9.2 Step 2 A dry 500 mL round bottomed flask was equipped with a stir bar and an argon inlet. The flask was charged with the crude diacid prepared in Step 1 (44 g) dissolved in MeOH (250 mL). To the reaction mixture was added chlorotrimethylsilane (80 mL, 630 mmol) portionwise. After stirring at room temperature for 15.5 h, the solution was concentrated to an oil and silica (5 g) was added. The mixture was suspended in MeOH (100 mL), and the volatiles were removed. Suspension in MeOH (100 mL) and the removal of the volatiles was repeated an additional two times. The residue was applied directly to the top of a flash chromatography column and was eluted hexanes/EtOAc 60:40 to yield dimethyl furan-2,3-dicarboxylate as an orange oil (38 g, 93% for Step 1 and Step 2 combined). 1H NMR (300 MHz, CDCl3) δ 3.81 (s, 3), 3.86 (s, 3), 6.71 (d, J=2.8, 1), 7.46 (d, J=2.8, 1); TLC (hexanes/EtOAc 60:40) Rf=0.46.

  • 18
  • [ 527-72-0 ]
  • [ 124-38-9 ]
  • [ 4282-24-0 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-thiophenylcarboxylic acid With n-butyllithium Inert atmosphere; Stage #2: carbon dioxide
  • 19
  • [ 4282-24-0 ]
  • diisopropyl 4,5,6,6a-tetrahydro-3aH-cyclopenta[b]furan-3a,6a-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sulfuric acid / toluene / 24 h / Reflux; Inert atmosphere 2.1: lithium trimethylstannyl / tetrahydrofuran / 1 h / -78 - -50 °C / Inert atmosphere 2.2: 21 h / -50 - 20 °C / Inert atmosphere
  • 20
  • [ 4282-24-0 ]
  • diisopropyl 3a,4,5,6,7,7a-hexahydrobenzofuran-3a,7a-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sulfuric acid / toluene / 24 h / Reflux; Inert atmosphere 2.1: lithium trimethylstannyl / tetrahydrofuran / 1 h / -78 - -50 °C / Inert atmosphere 2.2: 21 h / -50 - 20 °C / Inert atmosphere
  • 21
  • [ 4282-24-0 ]
  • diisopropyl 4,5,6,7,8,8a-hexahydro-3aH-cyclohepta[b]furan-3a,8adicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sulfuric acid / toluene / 24 h / Reflux; Inert atmosphere 2.1: lithium trimethylstannyl / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 2.2: 20 h / -78 - 40 °C / Inert atmosphere
  • 22
  • [ 4282-24-0 ]
  • [ 67-63-0 ]
  • [ 1374411-00-3 ]
YieldReaction ConditionsOperation in experiment
70% With sulfuric acid In toluene for 24h; Reflux; Inert atmosphere;
  • 23
  • [ 88-14-2 ]
  • [ 124-38-9 ]
  • [ 3238-40-2 ]
  • [ 4282-24-0 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-furanoic acid With n-butyllithium In tetrahydrofuran at -78℃; Stage #2: carbon dioxide at -78℃;
  • 24
  • [ 4282-24-0 ]
  • [ 13177-70-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: chloro-trimethyl-silane / 15.5 h / 20 °C 2.1: ethanol; water; hydrazine / 5.5 h / Heating / reflux 2.2: 4 h / Heating / reflux 3.1: pyridine; trichlorophosphate / 4 h / Heating / reflux
Multi-step reaction with 3 steps 1: chloro-trimethyl-silane / 15.5 h / 20 °C 2: hydrazine / ethanol / 5.5 h / Heating / reflux 3: pyridine; trichlorophosphate / 4 h / Heating / reflux
  • 25
  • [ 4282-24-0 ]
  • N-(4-chlorophenyl)-7-(4-pyridinylmethoxy)-furo[2,3-d]pyridazin-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: chloro-trimethyl-silane / 15.5 h / 20 °C 2.1: ethanol; water; hydrazine / 5.5 h / Heating / reflux 2.2: 4 h / Heating / reflux 3.1: pyridine; trichlorophosphate / 4 h / Heating / reflux 4.1: ethanol / 4 h / Heating / reflux 5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 24 h / 125 °C
Multi-step reaction with 5 steps 1: chloro-trimethyl-silane / 15.5 h / 20 °C 2: hydrazine / ethanol / 5.5 h / Heating / reflux 3: pyridine; trichlorophosphate / 4 h / Heating / reflux 4: ethanol / 4 h / Heating / reflux 5: 1,8-diazabicyclo[5.4.0]undec-7-ene / 24 h / 125 °C
  • 26
  • [ 4282-24-0 ]
  • [ 332012-45-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: chloro-trimethyl-silane / 15.5 h / 20 °C 2.1: ethanol; water; hydrazine / 5.5 h / Heating / reflux 2.2: 4 h / Heating / reflux 3.1: pyridine; trichlorophosphate / 4 h / Heating / reflux 4.1: ethanol / 2 h / Heating / reflux 5.1: sodium hydride / tetrahydrofuran / 0.33 h / 0 °C 5.2: 14 h / 0 - 20 °C
Multi-step reaction with 5 steps 1: chloro-trimethyl-silane / 15.5 h / 20 °C 2: hydrazine / ethanol / 5.5 h / Heating / reflux 3: pyridine; trichlorophosphate / 4 h / Heating / reflux 4: ethanol / 2 h / 95 °C 5: sodium hydride / tetrahydrofuran / 14 h / 0 - 20 °C
  • 27
  • [ 4282-24-0 ]
  • [ 332012-57-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: chloro-trimethyl-silane / 15.5 h / 20 °C 2.1: ethanol; water; hydrazine / 5.5 h / Heating / reflux 2.2: 4 h / Heating / reflux 3.1: pyridine; trichlorophosphate / 4 h / Heating / reflux 4.1: 1,2-dimethoxyethane; water / 48 h / 65 °C 5.1: 18-crown-6 ether / toluene / 0.17 h / 20 °C 5.2: 24 h / 80 °C
Multi-step reaction with 4 steps 1: chloro-trimethyl-silane / 15.5 h / 20 °C 2: hydrazine / ethanol / 5.5 h / Heating / reflux 3: 1,2-dimethoxyethane; water / 48 h / 65 °C 4: potassium hydroxide; 18-crown-6 ether / toluene / 24 h / 80 °C
  • 28
  • [ 4282-24-0 ]
  • [ 332012-40-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: chloro-trimethyl-silane / 15.5 h / 20 °C 2.1: ethanol; water; hydrazine / 5.5 h / Heating / reflux 2.2: 4 h / Heating / reflux 3.1: pyridine; trichlorophosphate / 4 h / Heating / reflux 4.1: ethanol / 4 h / Heating / reflux 5.1: potassium hydroxide; 18-crown-6 ether / toluene / 83 - 87 °C
Multi-step reaction with 5 steps 1: chloro-trimethyl-silane / 15.5 h / 20 °C 2: hydrazine / ethanol / 5.5 h / Heating / reflux 3: pyridine; trichlorophosphate / 4 h / Heating / reflux 4: ethanol / 4 h / Heating / reflux 5: potassium hydroxide; 18-crown-6 ether / toluene / 20 - 85 °C
  • 29
  • [ 4282-24-0 ]
  • [ 332012-40-5 ]
  • [ 332012-41-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: chloro-trimethyl-silane / 15.5 h / 20 °C 2.1: ethanol; water; hydrazine / 5.5 h / Heating / reflux 2.2: 4 h / Heating / reflux 3.1: pyridine; trichlorophosphate / 4 h / Heating / reflux 4.1: ethanol / 4 h / Heating / reflux 5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 24 h / 125 °C 6.1: sulfuric acid; iron(II) sulfate; hydroxylamine-O-sulfonic acid / water / 1.83 h / 20 °C 6.2: 0.17 h / 0 °C
Multi-step reaction with 6 steps 1: chloro-trimethyl-silane / 15.5 h / 20 °C 2: hydrazine / ethanol / 5.5 h / Heating / reflux 3: pyridine; trichlorophosphate / 4 h / Heating / reflux 4: ethanol / 4 h / Heating / reflux 5: 1,8-diazabicyclo[5.4.0]undec-7-ene / 24 h / 125 °C 6: sulfuric acid; iron(II) sulfate; hydroxylamine-O-sulfonic acid / water / 1.67 h / 20 °C
  • 30
  • [ 4282-24-0 ]
  • [ 332012-46-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: chloro-trimethyl-silane / 15.5 h / 20 °C 2.1: ethanol; water; hydrazine / 5.5 h / Heating / reflux 2.2: 4 h / Heating / reflux 3.1: pyridine; trichlorophosphate / 4 h / Heating / reflux 4.1: 1,2-dimethoxyethane; water / 48 h / 50 - 65 °C 5.1: 18-crown-6 ether / toluene / 0.17 - 0.33 h / 20 °C 5.2: 24 - 36 h / 80 °C
Multi-step reaction with 5 steps 1: chloro-trimethyl-silane / 15.5 h / 20 °C 2: hydrazine / ethanol / 5.5 h / Heating / reflux 3: pyridine; trichlorophosphate / 4 h / Heating / reflux 4: 1,2-dimethoxyethane; water / 48 h / 50 °C 5: potassium hydroxide; 18-crown-6 ether / toluene / 36 h / 80 °C
  • 31
  • [ 4282-24-0 ]
  • [ 332013-24-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: chloro-trimethyl-silane / 15.5 h / 20 °C 2.1: ethanol; water; hydrazine / 5.5 h / Heating / reflux 2.2: 4 h / Heating / reflux 3.1: pyridine; trichlorophosphate / 4 h / Heating / reflux 4.1: ethanol / 4 h / Heating / reflux 5.1: potassium hydroxide; 18-crown-6 ether / toluene / 83 - 87 °C 6.1: methanol / 0.08 h 6.2: 0.83 h / 0 °C
Multi-step reaction with 7 steps 1.1: chloro-trimethyl-silane / 15.5 h / 20 °C 2.1: ethanol; water; hydrazine / 5.5 h / Heating / reflux 2.2: 4 h / Heating / reflux 3.1: pyridine; trichlorophosphate / 4 h / Heating / reflux 4.1: ethanol / 4 h / Heating / reflux 5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 24 h / 125 °C 6.1: sulfuric acid; iron(II) sulfate; hydroxylamine-O-sulfonic acid / water / 1.83 h / 20 °C 6.2: 0.17 h / 0 °C 7.1: methanol / 0.08 h 7.2: 0.83 h / 0 °C
Multi-step reaction with 6 steps 1: chloro-trimethyl-silane / 15.5 h / 20 °C 2: hydrazine / ethanol / 5.5 h / Heating / reflux 3: pyridine; trichlorophosphate / 4 h / Heating / reflux 4: ethanol / 4 h / Heating / reflux 5: potassium hydroxide; 18-crown-6 ether / toluene / 20 - 85 °C 6: methanol; diethyl ether / 0.92 h / 0 °C
Multi-step reaction with 7 steps 1: chloro-trimethyl-silane / 15.5 h / 20 °C 2: hydrazine / ethanol / 5.5 h / Heating / reflux 3: pyridine; trichlorophosphate / 4 h / Heating / reflux 4: ethanol / 4 h / Heating / reflux 5: 1,8-diazabicyclo[5.4.0]undec-7-ene / 24 h / 125 °C 6: sulfuric acid; iron(II) sulfate; hydroxylamine-O-sulfonic acid / water / 1.67 h / 20 °C 7: methanol; diethyl ether / 0.92 h / 0 °C

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