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Cas:321-14-2
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inquiryProduct Name: 5-Chloro-2-hydroxybenzoic acid Synonyms: 5-chloro-2-hydroxybenzoate;5-chloro-salicylicaci;Benzoic acid, 5-chloro-2-hydroxy-;Salicylic acid, 5-chloro-;CHLOROSALICYLIC(5-) ACID;5-CHLOROSALICYLIC ACID;5-CHLOROSALICYCLIC ACID;5-CHLORO-2-
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Conditions | Yield |
---|---|
Stage #1: 4-chloro-phenol With sodium hydroxide In water for 2h; Autoclave; Reflux; Stage #2: carbon dioxide In N,N-dimethyl-formamide at 80 - 145℃; under 2250.23 - 3750.38 Torr; for 15h; Autoclave; Stage #3: With sulfuric acid In 5,5-dimethyl-1,3-cyclohexadiene pH=6.5; | 97.65% |
Stage #1: 4-chloro-phenol With Mesitol; sodium hydride In mineral oil at 100℃; for 0.0833333h; Glovebox; Stage #2: carbon dioxide In mineral oil at 185℃; under 760.051 Torr; for 2h; | 85% |
With potassium carbonate at 140℃; under 29420.3 Torr; |
Conditions | Yield |
---|---|
With oxygen; potassium acetate; palladium diacetate; p-benzoquinone In N,N-dimethyl acetamide at 115℃; under 3800.26 Torr; for 15h; | 95% |
With oxygen; potassium acetate; p-benzoquinone; palladium diacetate In ISOPROPYLAMIDE at 115℃; under 3800.26 Torr; for 15h; Product distribution / selectivity; | 95% |
Multi-step reaction with 2 steps 1: fuming nitric acid / Reduzieren des Nitrierungsprodukts mit Zinn und Salzsaeure 2: water; nitrous acid View Scheme |
Conditions | Yield |
---|---|
Stage #1: salicylic acid With sulfuric acid In acetonitrile at 20℃; for 0.0833333h; Stage #2: With N-chloro-succinimide In acetonitrile at 20℃; for 2.5h; regioselective reaction; | 92% |
With sodium periodate; sulfuric acid; sodium dodecyl-sulfate; acetic acid; sodium chloride In water at 25℃; for 2h; | 85% |
With hydrogenchloride; sodium percarbonate; dihydrogen peroxide In dichloromethane; water at 40 - 45℃; Reagent/catalyst; Solvent; Green chemistry; | 82.5% |
Conditions | Yield |
---|---|
With pyridine; water; potassium carbonate; copper for 0.25h; sonication; | 92% |
With pyridine; copper; potassium carbonate In water for 2h; Heating; | 84% |
With sodium methylate at 150℃; Eintragen des Reaktionsgemisches in Wasser; | |
With copper(l) iodide; copper; potassium carbonate at 170℃; under 4413.05 Torr; |
Conditions | Yield |
---|---|
With carbon dioxide at 190℃; under 7600.51 Torr; for 6h; Time; Temperature; Pressure; Autoclave; regioselective reaction; | 86.1% |
2-bromo-5-chlorobenzoic acid
5-chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
With copper(I) oxide; 2-pyridinealdoxime; cesium hydroxide; tetrabutylammomium bromide In water at 100℃; for 48h; Inert atmosphere; | 81% |
6-chloro-2-methyl-4H-chromen-4-one
5-chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
With potassium permanganate beim Erwaermen mit Jodwasserstoffsaeure; |
5-chloro-2-hydroxybenzonitrile
5-chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
With sulfuric acid; water at 200℃; |
Conditions | Yield |
---|---|
With sulfuryl dichloride; benzene |
Conditions | Yield |
---|---|
With sodium hydroxide |
Conditions | Yield |
---|---|
With tetrachloromethane; potassium hydroxide; ethanol at 140℃; im geschlossenen Rohr; | |
Multi-step reaction with 4 steps 1.1: 1H-imidazole / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: water; sodium hydrogencarbonate / N,N-dimethyl-formamide; diethyl ether / 0.5 h / 20 °C / Inert atmosphere 3.1: palladium diacetate; silver(I) acetate; N-tert-butoxycarbonyl-L-leucine; 2,2,2-trifluoroethanol / 1,2-dichloro-ethane / 0.08 h / 95 °C / Inert atmosphere 3.2: 18 h / 95 °C / Inert atmosphere 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / Inert atmosphere View Scheme | |
With oxygen; potassium acetate; palladium diacetate; p-benzoquinone In N,N-dimethyl acetamide at 115℃; for 15h; Schlenk technique; regioselective reaction; | |
With tetrachloromethane; sodium hydroxide; copper |
Conditions | Yield |
---|---|
With water; cis-nitrous acid |
N,N-dichloro-p-toluenesulfonamide
salicylic acid
5-chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
With chloroform |
salicylic acid
A
5-chloro-2-hydroxybenzoic acid
B
3,5-dichlorosalicylic acid
Conditions | Yield |
---|---|
With ethanol; chlorine | |
With tert-butylhypochlorite In water | |
With ethanol beim Chlorieren; Trennung ueber die Bariumsalze; | |
With antimonypentachloride |
salicylic acid
A
5-chloro-2-hydroxybenzoic acid
B
3-Chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
With sodium carbonate bei der Chlorierung; | |
With sodium hydroxide; sodium hypochlorite at 20℃; for 2.5h; pH > 12; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
With N-chlorotriethylammonium chloride In trifluoroacetic acid Ambient temperature; Yield given. Yields of byproduct given; |
Conditions | Yield |
---|---|
With sulfuryl dichloride Behandeln mit Kalilauge; |
Conditions | Yield |
---|---|
With sodium hydroxide; alpha cyclodextrin In water at 25℃; Rate constant; Ionic strength: 1.0 (NaCl); effect of pH, concentration of α-cyclodextrin; | |
With water at 25℃; Kinetics; |
4-chlorosalicylate
5-chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
In ethanol; water at 25℃; Equilibrium constant; |
6-chloro-2-methyl-4H-chromen-4-one
5-chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
With sodium hydroxide; dihydrogen peroxide In methanol at 20℃; Oxidation; | |
Multi-step reaction with 2 steps 1: 59 percent / AcONa / 2 h / 260 - 270 °C 2: 10 percent aq. NaOH / ethanol / 4 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: 88 percent / Na / diethyl ether 2: 10 percent aq. KOH View Scheme |
3-(6-chloro-4-oxo-4H-chromen-2-yl)-2-oxo-propionic acid ethyl ester
5-chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
With potassium hydroxide Hydrolysis; |
6-Chloro-2-(3-phthalidenemethylene)chromone
A
5-chloro-2-hydroxybenzoic acid
B
benzene-1,2-dicarboxylic acid
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol for 4h; Hydrolysis; Heating; |
6-chloro-2,3-dimethyl-chromen-4-one
5-chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
beim Schmelzen; |
water
cis-nitrous acid
5-chloroanthranilic acid
5-chloro-2-hydroxybenzoic acid
chlorine
nitrobenzene
salicylic acid
5-chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
bei Siedetemperatur; |
tetrachloromethane
ethanol
4-chloro-phenol
5-chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
at 140℃; |
Conditions | Yield |
---|---|
Stage #1: 5-chloro-2-hydroxybenzoic acid With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 65℃; for 0.0833333h; Inert atmosphere; Stage #2: 3-Chloro-2-methylpropene In N,N-dimethyl-formamide at 65℃; for 21h; | 100% |
With potassium carbonate In N-methyl-acetamide |
5-chloro-2-hydroxybenzoic acid
2-Methylphenylboronic acid
4-hydroxy-2'-methylbiphenyl-3-carboxylic acid
Conditions | Yield |
---|---|
With sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐3‐sulfonate; palladium diacetate; potassium carbonate In water at 20℃; for 12h; Suzuki-Miyaura coupling; | 99% |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In diethyl ether for 0.75h; Heating; | 97% |
With sodium tetrahydroborate; Trimethyl borate; dimethyl sulfate In tetrahydrofuran at 20℃; for 4.5h; | 96% |
With borane-THF; boron trifluoride diethyl etherate In tetrahydrofuran at 20℃; for 18h; | 85% |
5-chloro-2-hydroxybenzoic acid
acetic anhydride
2-acetoxy-5-chloro-benzoic acid
Conditions | Yield |
---|---|
With sulfuric acid for 3h; Heating / reflux; | 97% |
With sulfuric acid | 93% |
With sulfuric acid | 93% |
Conditions | Yield |
---|---|
Stage #1: 5-chloro-2-hydroxybenzoic acid With potassium hydroxide In methanol at 20℃; for 1h; Stage #2: tributyltin chloride In methanol for 5h; | 97% |
zirconocene dichloride
5-chloro-2-hydroxybenzoic acid
[Cp2Zr(μ2-O',O''C-C6H3(OH)Cl)2]
Conditions | Yield |
---|---|
In hydrogenchloride; dichloromethane mixt. of zirconocene dichloride in 1 M aq. HCl and dichlorobenzoic acidin CH2Cl2 was stirred for 30 min at room temp.; organic layer was separated, dried over MgSO4, filtered, concd. in vac.,crystd. form CH2Cl2/Et2O/hexane, elem. anal.; | 96.3% |
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid at 20℃; | 96% |
With sulfuric acid; nitric acid at 0 - 20℃; for 5.66667h; | 95% |
With sulfuric acid; nitric acid for 6h; Ambient temperature; | 90.5% |
Conditions | Yield |
---|---|
With bromine In chloroform | 96% |
With N-Bromosuccinimide In carbon disulfide at 25℃; for 14h; | |
With bromine; acetic acid at 80℃; for 8h; | 204.6 g |
With bromine; acetic acid at 80℃; for 8h; | 204.6 g |
dichloromethane
5-chloro-2-hydroxybenzoic acid
6-chloro-4H-benzo[d][1,3]dioxin-4-one
Conditions | Yield |
---|---|
With potassium phosphate tribasic trihydrate In N,N-dimethyl-formamide at 100℃; under 760.051 Torr; for 6h; Green chemistry; | 96% |
5-chloro-2-hydroxybenzoic acid
5,5-dibenzyl-2,3,4,5-tetrahydropyridine
Conditions | Yield |
---|---|
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In toluene at 90℃; for 20h; | 96% |
5-chloro-2-hydroxybenzoic acid
acetyl chloride
2-acetoxy-5-chloro-benzoic acid
Conditions | Yield |
---|---|
With pyridine; sulfuric acid In toluene | 95.6% |
With triethylamine In tetrahydrofuran at 20℃; | 46.7% |
Conditions | Yield |
---|---|
Stage #1: sebacoyl chloride; 5-chloro-2-hydroxybenzoic acid With pyridine In tetrahydrofuran for 2h; Stage #2: With hydrogenchloride In tetrahydrofuran; water pH=2; | 95% |
Conditions | Yield |
---|---|
Stage #1: 5-chloro-2-hydroxybenzoic acid With potassium hydroxide In methanol at 20℃; for 1h; Stage #2: dibutyltin chloride In methanol for 5h; | 95% |
5-chloro-2-hydroxybenzoic acid
2,4-difluorophenylboronic acid
2',4'-difluoro-4-hydroxybiphenyl-3-carboxylic acid
Conditions | Yield |
---|---|
With bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II); tetrabutylammomium bromide; potassium carbonate In ethanol; water for 8h; Concentration; Reagent/catalyst; Suzuki Coupling; Inert atmosphere; Reflux; | 95% |
5-chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
With pyridine; dicyclohexyl-carbodiimide at 80℃; for 2h; Microwave irradiation; | 95% |
Conditions | Yield |
---|---|
With sulfuric acid In methanol | 94.8% |
With thionyl chloride In methanol; ethyl acetate | 74% |
With thionyl chloride In methanol; ethyl acetate | 74% |
Conditions | Yield |
---|---|
In methanol | 94.8% |
methanol
5-chloro-2-hydroxybenzoic acid
methyl 5-chloro-2-hydroxybenzoate
Conditions | Yield |
---|---|
With thionyl chloride for 168h; Inert atmosphere; Reflux; | 94% |
With sulfuric acid for 120h; Inert atmosphere; Reflux; | 91% |
With sulfuric acid for 120h; Reflux; | 91% |
Conditions | Yield |
---|---|
Stage #1: 5-chloro-2-hydroxybenzoic acid With potassium hydroxide In methanol at 20℃; for 1h; Stage #2: triphenyltin chloride In methanol for 5h; | 94% |
2-fluoroethyl bromide
5-chloro-2-hydroxybenzoic acid
2-fluoroethyl 5-chloro-2-(2-fluoroethoxy)benzoate
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 80℃; for 48h; | 93.4% |
With sodium hydride |
bis(3-bromopropyl) ether
5-chloro-2-hydroxybenzoic acid
5-chloro-2-(2-methoxyethoxy)benzoic acid 2-methoxyethyl ester
Conditions | Yield |
---|---|
With potassium carbonate In ethyl acetate; acetonitrile | 93% |
5-chloro-2-hydroxybenzoic acid
Conditions | Yield |
---|---|
Stage #1: 5-chloro-2-hydroxybenzoic acid With sodium hydroxide In water Stage #2: copper dichloride In water for 24h; | 93% |
5-chloro-2-hydroxybenzoic acid
4-cyanophenylboronic acid
Conditions | Yield |
---|---|
With sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐3‐sulfonate; palladium diacetate; potassium carbonate In water at 80℃; for 12h; Suzuki-Miyaura coupling; | 92% |
Conditions | Yield |
---|---|
Stage #1: 5-chloro-2-hydroxybenzoic acid With potassium hydroxide In methanol at 20℃; for 1h; Stage #2: dibutyltin chloride In methanol for 5h; | 92% |
bis(cyclopentadienyl)titanium dichloride
5-chloro-2-hydroxybenzoic acid
Ti(η5-C5H5)2(C6H3Cl(O)(CO2))
Conditions | Yield |
---|---|
With NaOH; catalyst: C2H5OH In ethanol; chloroform; water-d2 Kinetics; NaOH and C2H5OH added to mixt. of (C5H5)2TiCl2 and acid dissolved in CHCl3, stirred for 30 min at room temp.; dried (anhydrous MgSO4), filtered, filtrate concd. in vac., ppt. recrystd. from CH2Cl2/hexane; elem. anal.; | 91.1% |
Conditions | Yield |
---|---|
Stage #1: 5-chloro-2-hydroxybenzoic acid With potassium hydroxide In methanol at 20℃; for 1h; Stage #2: trimethyltin(IV)chloride In methanol for 5h; | 91% |
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