2,3-dihydroxybenzaldehyde
2,3-Dihydroxybenzoic acid
Conditions | Yield |
---|---|
With dihydrogen peroxide In water; acetonitrile at 45℃; for 12h; chemoselective reaction; | 82% |
Conditions | Yield |
---|---|
With lithium hydroxide In ethanol; water at 25℃; for 2h; | 71% |
benzoic acid
A
2,3-Dihydroxybenzoic acid
B
2,5-dihydroxybenzoic acid.
C
3-Carboxyphenol
D
salicylic acid
E
4-hydroxy-benzoic acid
Conditions | Yield |
---|---|
With oxygen; iron(II) sulfate In water at 40℃; for 3h; Product distribution; pH 6.8 buffer; | A 9% B 5% C 14% D 4% E 9% |
benzoic acid
A
2,3-Dihydroxybenzoic acid
B
2,5-dihydroxybenzoic acid.
C
3-Carboxyphenol
D
4-hydroxy-benzoic acid
Conditions | Yield |
---|---|
With oxygen; iron(II) sulfate In water at 40℃; for 3h; Further byproducts given; | A 9% B 5% C 14% D 9% |
Conditions | Yield |
---|---|
With sodium hydroxide; dihydrogen peroxide |
Conditions | Yield |
---|---|
With potassium carbonate beim Schmelzen; |
Conditions | Yield |
---|---|
With aluminium trichloride; chlorobenzene | |
With hydrogenchloride at 140℃; im Rohr; | |
With aluminium trichloride at 150℃; | |
With hydrogen bromide at 110 - 120℃; |
Conditions | Yield |
---|---|
With hydrogen iodide at 100℃; | |
Multi-step reaction with 5 steps 1: N,N-dimethyl-formamide; thionyl chloride / dichloromethane / 2 h / 30 - 35 °C 2: ammonium hydroxide / dichloromethane; water / 0.5 h / -5 - 35 °C 3: trichlorophosphate / toluene / 30 - 85 °C 4: triethylamine; aluminum (III) chloride / toluene / 9.5 h / 30 - 75 °C 5: water; hydrogenchloride / toluene / 0.5 h / 15 - 35 °C View Scheme |
2-iodo-3-hydroxybenzaldehyde
2,3-Dihydroxybenzoic acid
Conditions | Yield |
---|---|
at 100℃; |
3-(benzyloxy)-2-hydroxybenzoic acid
2,3-Dihydroxybenzoic acid
Conditions | Yield |
---|---|
With hydrogen bromide at 100 - 110℃; |
Conditions | Yield |
---|---|
With ammonium carbonate; water at 130 - 140℃; im geschlossenen Rohr; |
Conditions | Yield |
---|---|
With potassium dicarbonate; glycerol at 180 - 210℃; | |
With potassium dicarbonate | |
With 2,6-dihydroxybenzoic acid decarboxylase from Rhizobium species; potassium hydrogencarbonate at 30℃; for 24h; pH=8.5; aq. phosphate buffer; Enzymatic reaction; regioselective reaction; |
Conditions | Yield |
---|---|
ueber mehrere Stufen; | |
With potassium hydroxide at 250℃; |
Conditions | Yield |
---|---|
Multistep reaction; |
Anguibactin
A
histamine
B
2,3-Dihydroxybenzoic acid
C
Dehydrocystine
Conditions | Yield |
---|---|
With hydrogenchloride at 100℃; for 24h; |
Conditions | Yield |
---|---|
With dihydrogen peroxide; methylene blue In ethanol at 25℃; Quantum yield; Irradiation; | |
With dihydrogen peroxide; methylene blue In ethanol at 25℃; Irradiation; | |
Multi-step reaction with 2 steps 1: alcohol; iodine 2: potash / beim Schmelzen View Scheme |
Conditions | Yield |
---|---|
With iron(III)-acetylacetonate; dihydrogen peroxide; methylene blue at 25℃; for 4h; Product distribution; Mechanism; Irradiation; other salicylic derivatives, hydroxylation; | |
With oxygen; potassium oxalate; iron(III) chloride In water at 25℃; Product distribution; Irradiation; role of hydrogen peroxide in dyoxygen induced hydroxylation of title compound; photochemicall and thermal (pH 7.1) hydroxylation; | |
With dihydrogen peroxide In water at 20℃; for 0.5h; Mechanism; Product distribution; Quantum yield; Irradiation; various pH value and reaction time, HClO4 or K2CO3 presence; |
Conditions | Yield |
---|---|
With Fe(III)(sal)3(3-); dihydrogen peroxide In water at 25℃; for 1h; Product distribution; Thermodynamic data; Irradiation; other times; presence of O2; |
2,2-dimethylbenzo[d][1,3]dioxole-4-carboxylic acid
2,3-Dihydroxybenzoic acid
Conditions | Yield |
---|---|
With sulfuric acid |
Conditions | Yield |
---|---|
With dihydrogen peroxide In acetonitrile Irradiation; |
2,3-Dihydroxybenzoic acid
Conditions | Yield |
---|---|
With β-glucosidase for 168h; Ambient temperature; enzymatic hydrolysis; |
salicylate
A
2,3-Dihydroxybenzoic acid
B
2,5-dihydroxybenzoic acid.
Conditions | Yield |
---|---|
With dihydrogen peroxide; potassium carbonate In water at 20℃; for 0.5h; Mechanism; Product distribution; Quantum yield; Irradiation; various pH value and reaction time; |
salicylic acid
A
4-hydroxysalicylic acid
B
2,3-Dihydroxybenzoic acid
C
2,5-dihydroxybenzoic acid.
D
2,6-Dihydroxybenzoic acid
Conditions | Yield |
---|---|
With dihydrogen peroxide; iron(II) sulfate In water at 37℃; for 0.0833333h; hydroxylation; Further byproducts given. Title compound not separated from byproducts; |
salicylic acid
A
formic acid
B
malic acid
C
2,3-Dihydroxybenzoic acid
D
oxalic acid
Conditions | Yield |
---|---|
With dihydrogen peroxide at 23℃; for 4h; pH=6.2; Oxidation; UV-irradiation; Further byproducts given; |
salicylic acid
A
cis,cis-Muconic acid
B
malonic acid
C
2,3-Dihydroxybenzoic acid
D
hydroquinone
Conditions | Yield |
---|---|
With dihydrogen peroxide at 23℃; for 2.5h; pH=6.2; Kinetics; Oxidation; UV-irradiation; |
sulfuric acid
3-(2,5-dimethoxy-tetrahydro-[2]furyl)-3-oxo-propionic acid methyl ester
A
methyl-2,3-dihydroxybenzoate
B
2,3-Dihydroxybenzoic acid
Conditions | Yield |
---|---|
at 160℃; |
Conditions | Yield |
---|---|
at 180 - 210℃; | |
at 180℃; |
Conditions | Yield |
---|---|
at 250℃; |
water
benzene-1,2-diol
A
3,4-Dihydroxybenzoic acid
B
2,3-Dihydroxybenzoic acid
Conditions | Yield |
---|---|
at 140℃; |
Conditions | Yield |
---|---|
sulfuric acid for 24h; Reflux; | 100% |
With sulfuric acid | |
With sulfuric acid |
2,3-Dihydroxybenzoic acid
p-toluenesulfonyl chloride
2-hydroxy-3-(toluene-4-sulfonyloxy)-benzoic acid
Conditions | Yield |
---|---|
With sodium hydroxide In water; acetone at 40℃; | 100% |
Conditions | Yield |
---|---|
With sulfuric acid for 6h; Reflux; | 100% |
With sulfuric acid at 0℃; for 12h; Heating / reflux; | 99% |
With thionyl chloride at 20℃; | 99% |
2,3-Dihydroxybenzoic acid
2,3-dihydroxy-5-bromobenzoic acid
Conditions | Yield |
---|---|
With bromine; acetic acid at 20℃; for 24h; | 99% |
With bromine In acetic acid at 20℃; for 16h; Inert atmosphere; regioselective reaction; | 99% |
With bromine In acetic acid at 20℃; | 88% |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In hydrogenchloride; methanol | 99% |
With sodium hydrogencarbonate In hydrogenchloride; methanol | 99% |
Conditions | Yield |
---|---|
sulfuric acid In diethyl ether for 12h; | 98% |
With sulfuric acid In diethyl ether at 20℃; for 12h; Esterification; | 91% |
With sulfuric acid for 0.416667h; Heating; | 74% |
2,3-Dihydroxybenzoic acid
benzyl bromide
benzyl 2,3-bis(benzyloxy)benzoate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide for 5h; Ambient temperature; | 98% |
With potassium carbonate In acetone for 24h; Inert atmosphere; Reflux; | 94% |
With potassium carbonate In acetone for 24h; Reflux; Inert atmosphere; | 81% |
Conditions | Yield |
---|---|
With sulfuric acid In methanol | 98% |
With sulfuric acid In methanol | |
With sulfuric acid In methanol; water | |
Multi-step reaction with 2 steps 1: thionyl chloride / 78 °C / Inert atmosphere 2: triethylamine / 16 h / 0 - 25 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: thionyl chloride / Reflux 2: triethylamine / chloroform / 18 h / Reflux View Scheme |
2,3-Dihydroxybenzoic acid
chlorure de 2,3-dioxosulfinylbenzoyle
Conditions | Yield |
---|---|
With thionyl chloride; urea at 40℃; for 3h; Cyclization; | 97% |
With thionyl chloride; urea at 40℃; for 2h; Yield given; | |
With thionyl chloride for 8h; Heating; |
Conditions | Yield |
---|---|
With sulfuric acid for 18h; Reflux; | 97% |
2,3-Dihydroxybenzoic acid
benzyl chloride
benzyl 2,3-bis(benzyloxy)benzoate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide Reflux; Inert atmosphere; | 96% |
With potassium carbonate In N,N-dimethyl-formamide at 90℃; | 91% |
2,3-Dihydroxybenzoic acid
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; methanesulfonic acid; iron(II) phthalocyanine; acetic acid In water; acetonitrile at 5℃; for 0.0833333h; | 96% |
2,3-Dihydroxybenzoic acid
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; methanesulfonic acid; iron(II) phthalocyanine; acetic acid In water; acetonitrile at 5℃; for 0.0833333h; | 96% |
1-hydroxy-pyrrolidine-2,5-dione
2,3-Dihydroxybenzoic acid
succinimido 2,3-dihydroxybenzoate.
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In 1,4-dioxane for 16h; | 95% |
Conditions | Yield |
---|---|
Stage #1: 2,3-Dihydroxybenzoic acid With sulfuric acid In methanol Stage #2: benzyl bromide With potassium carbonate In methanol; chloroform Stage #3: With barium(II) hydroxide In tetrahydrofuran; water at 50℃; | 95% |
Stage #1: 2,3-Dihydroxybenzoic acid; benzyl bromide With potassium carbonate In acetone for 24h; Reflux; Stage #2: With lithium hydroxide In methanol; water for 3h; Reflux; Stage #3: With hydrogenchloride In methanol; water at 0℃; | 91% |
With potassium hydroxide In dimethyl sulfoxide for 4h; | 89% |
morpholine
2,3-Dihydroxybenzoic acid
lead(II) thiocyanate
8-hydroxy-2-morpholin-4-yl-4H-1,3-benzoxazin-4-one
Conditions | Yield |
---|---|
Stage #1: 2,3-Dihydroxybenzoic acid; lead(II) thiocyanate With dibromotriphenylphosphorane In tetrahydrofuran; dichloromethane at 0 - 20℃; for 4h; Inert atmosphere; Reflux; Stage #2: morpholine In 1,4-dioxane for 4h; Reflux; | 95% |
2,3-Dihydroxybenzoic acid
isopropyl bromide
2,3-diisopropyloxybenzoic acid
Conditions | Yield |
---|---|
Stage #1: 2,3-Dihydroxybenzoic acid; isopropyl bromide With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 50℃; Stage #2: With barium(II) hydroxide In tetrahydrofuran; water at 50℃; | 95% |
2,3-Dihydroxybenzoic acid
benzoic acid anhydride
2,3-Dibenzyloxybenzoic acid
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 20℃; for 16h; | 93% |
Conditions | Yield |
---|---|
With sodium acetate; potassium hexacyanoferrate(III) In water at 20℃; for 0.166667h; | 92% |
2,3-Dihydroxybenzoic acid
p-methoxybenzyl chloride
4-methoxybenzyl 2,3-bis((4-methoxybenzyl)oxy)benzoate
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In acetone for 72h; Inert atmosphere; Reflux; | 92% |
Stage #1: 2,3-Dihydroxybenzoic acid With tetra-(n-butyl)ammonium iodide; potassium carbonate In acetone at 25℃; for 1h; Stage #2: p-methoxybenzyl chloride In acetone Reflux; | 70% |
With potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 70℃; for 2h; | 52% |
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 2h; Inert atmosphere; | 52% |
2,3-Dihydroxybenzoic acid
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; methanesulfonic acid; iron(II) phthalocyanine; acetic acid In water; acetonitrile at 5℃; for 0.5h; | 91% |
2,3-Dihydroxybenzoic acid
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; methanesulfonic acid; iron(II) phthalocyanine; acetic acid In water; acetonitrile at 5℃; for 0.166667h; | 91% |
2,3-Dihydroxybenzoic acid
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; methanesulfonic acid; iron(II) phthalocyanine; acetic acid In water; acetonitrile at 5℃; for 0.166667h; | 91% |
Conditions | Yield |
---|---|
With sodium acetate; potassium hexacyanoferrate(III) In water for 1h; Michael addition reaction; | 90% |
N-BOC-1,2-diaminoethane
2,3-Dihydroxybenzoic acid
N-(N'-tert-butyloxycarbonylethanediamino)-2,3-bis(benzyloxy)benzamide
Conditions | Yield |
---|---|
Stage #1: 2,3-Dihydroxybenzoic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 25℃; for 0.25h; Stage #2: N-BOC-1,2-diaminoethane In N,N-dimethyl-formamide at 25℃; for 0.5h; | 90% |
2,3-Dihydroxybenzoic acid
Conditions | Yield |
---|---|
With trichlorophosphate at 120℃; | 89.3% |
Conditions | Yield |
---|---|
In toluene for 1h; Sealed tube; Heating; | 89% |
2,3-Dihydroxybenzoic acid
Conditions | Yield |
---|---|
In water tungstic acid, 2,3-dihydroxybenzoic acid, Me4NOH refluxed overnight in H2O; hot filtered; evapd. to dryness; washed with hot THF, CH2Cl2, Et2O; vac.dried at 70°C; | 87% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 1h; | 86% |
2,3-Dihydroxybenzoic acid
Conditions | Yield |
---|---|
With trichlorophosphate Reflux; | 86% |
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