Conditions | Yield |
---|---|
With silica gel; 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium perchlorate In dichloromethane | 100% |
With manganese(IV) oxide; manganese(II) nitrate tetrahydrate; dibenzoyl peroxide In hexane at 70℃; under 760.051 Torr; for 0.0833333h; chemoselective reaction; | 99% |
In neat (no solvent) at 20℃; for 0.0333333h; Microwave irradiation; | 99% |
meta-hydroxybenzaldehyde
Conditions | Yield |
---|---|
With hydrogenchloride for 0.0416667h; Product distribution; Ambient temperature; pH = 4-6, regeneration of aldehyde; | 100% |
Conditions | Yield |
---|---|
With iron(III) chloride on silica In neat (no solvent) at 80℃; for 0.5h; | 99% |
With magnesium iodide for 5h; neat (no solvent); | 93% |
3-(tert-butyl-dimethyl-sylanyloxy)benzaldehyde
meta-hydroxybenzaldehyde
Conditions | Yield |
---|---|
With lithium acetate In water; N,N-dimethyl-formamide at 25℃; for 8h; Inert atmosphere; | 96% |
With triethylamine N-oxide In methanol for 1h; | 91% |
In water; dimethyl sulfoxide at 90℃; for 8h; | 87% |
2-(3-hydroxyphenyl)-1,3-dithiolane
meta-hydroxybenzaldehyde
Conditions | Yield |
---|---|
With ammonium iodide; dihydrogen peroxide; sodium dodecyl-sulfate In water at 20℃; for 1h; micellar medium; | 96% |
With 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one; dihydrogen peroxide In water; acetonitrile at 20℃; for 1h; | 94% |
With dihydrogen peroxide; iodine; sodium dodecyl-sulfate In water at 20℃; for 3h; Micellar solution; | 90% |
2-(3-hydroxyphenyl)-1,3-dithiane
meta-hydroxybenzaldehyde
Conditions | Yield |
---|---|
With dihydrogen peroxide; iodine; sodium dodecyl-sulfate In water at 20℃; for 0.666667h; Micellar solution; | 95% |
With acetic acid at 25℃; for 15h; | 51% |
3-benzenesulfonyloxy-benzaldehyde
meta-hydroxybenzaldehyde
Conditions | Yield |
---|---|
With potassium hydroxide In toluene; tert-butyl alcohol at 100℃; for 0.5h; Inert atmosphere; | 95% |
3-Formylphenylboronic acid
meta-hydroxybenzaldehyde
Conditions | Yield |
---|---|
With C100H52N4O16Sn(6-)*2In(3+); N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 3.5h; Irradiation; | 94% |
With C18H28Cl2CuN2O4 In water at 26℃; for 0.333333h; | 92% |
With 10-methylacridine-3(10H)-one; oxygen; N-ethyl-N,N-diisopropylamine In water at 20℃; for 20h; Irradiation; Green chemistry; | 90% |
3-allyloxy-benzaldehyde
meta-hydroxybenzaldehyde
Conditions | Yield |
---|---|
With bis(benzonitrile)palladium(II) dichloride In benzene for 20h; Heating; | 92% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In methanol at 20℃; for 6h; | 82% |
3-((triisopropylsilyl)oxy)benzaldehyde
meta-hydroxybenzaldehyde
Conditions | Yield |
---|---|
With potassium acetate In water; N,N-dimethyl-formamide at 25℃; for 13h; | 92% |
Conditions | Yield |
---|---|
With oxygen; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 12h; | 92% |
3-hydroxybenzaldehyde oxime
meta-hydroxybenzaldehyde
Conditions | Yield |
---|---|
With N,N'-dichlorophenobarbital In acetonitrile at 20℃; | 92% |
With iodine at 45 - 60℃; for 0.2h; Reagent/catalyst; Microwave irradiation; | 83% |
Conditions | Yield |
---|---|
With bis(η3-allyl-μ-chloropalladium(II)); t-BuBrettPhos; p-methylbenzaldehyde oxime; caesium carbonate In N,N-dimethyl-formamide at 90℃; for 2h; Inert atmosphere; | 92% |
With nickel(II) sulphate; water; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 12h; pH=8.8; UV-irradiation; Inert atmosphere; Glovebox; Enzymatic reaction; | 70 %Spectr. |
meta-hydroxybenzaldehyde
Conditions | Yield |
---|---|
With tribromo-isocyanuric acid In acetonitrile for 1.5h; Reflux; | 90% |
Conditions | Yield |
---|---|
With magnesium iodide for 5h; neat (no solvent); | 89% |
With 1-methyl-pyrrolidin-2-one; potassium carbonate at 190℃; for 0.5h; | 85% |
With 1-methyl-pyrrolidin-2-one; potassium carbonate; thiophenol for 0.5h; Heating; | 85% |
3-(4-Methoxybenzyloxy)benzaldehyde
A
p-methoxybenzyl acetate
B
meta-hydroxybenzaldehyde
Conditions | Yield |
---|---|
With acetic acid at 90℃; for 24h; | A n/a B 88% |
Acetic acid acetoxy-(3-hydroxy-phenyl)-methyl ester
meta-hydroxybenzaldehyde
Conditions | Yield |
---|---|
With ammonium cerium(IV) nitrate In acetonitrile at 70℃; for 5.5h; | 88% |
With formic acid; water; sodium dodecyl-sulfate for 4h; Heating; | 80% |
Conditions | Yield |
---|---|
With iodine; triethylamine; triphenylphosphine In toluene at 80℃; for 2h; Sealed tube; | 88% |
With iodine; triethylamine; triphenylphosphine In toluene at 80℃; Inert atmosphere; Sealed tube; | 88% |
N-(2,4-dinitrophenyl)-N'-(3'-hydroxybenzylidene)hydrazone
meta-hydroxybenzaldehyde
Conditions | Yield |
---|---|
With 1,4-dichloro-1,4-diazoniabicyclo[2,2,2]octane bischloride In water at 50℃; for 0.25h; pH=7; | 86% |
3-Hydroxybenzyl alcohol
A
(m-hydroxybenzyl) methyl ether
B
meta-hydroxybenzaldehyde
C
3-Carboxyphenol
Conditions | Yield |
---|---|
With sodium hydroxide; oxygen; platinum on activated charcoal; cerium(III) chloride; bismuth(III) sulfate In methanol; water at 50℃; for 2h; | A 5 % Chromat. B 83% C 1 % Chromat. |
With sodium hydroxide; oxygen; platinum on activated charcoal; bismuth(III) sulfate In methanol; water at 50℃; for 2h; | A 6 % Chromat. B 71 % Chromat. C 18 % Chromat. |
With sodium hydroxide; oxygen; platinum on activated charcoal; cerium(III) chloride; bismuth(III) sulfate In methanol; water at 50℃; for 2h; Product distribution; further solvent: water; further catalyst: 3percent Pt/C, Bi2(SO4)3; | A 6 % Chromat. B 71 % Chromat. C 18 % Chromat. |
Conditions | Yield |
---|---|
With tetrabutylammonium tetrafluoroborate; tris(2,2'-bipyridine)nickel(II) tetrafluoroborate In N,N-dimethyl-formamide electrochem. reaction; magnesium rod anode, nickel foam grid cathode; | 83% |
meta-hydroxybenzaldehyde
Conditions | Yield |
---|---|
With copper(II) nitrate hexahydrate In dichloromethane; water at 20℃; for 5h; | 83% |
Conditions | Yield |
---|---|
With poly(4-vinylpyridinium) hydrogen sulfate solid acid In methanol at 20℃; for 0.633333h; Irradiation; | 82% |
3-hydroxybenzoyl chloride
meta-hydroxybenzaldehyde
Conditions | Yield |
---|---|
With palladium on activated charcoal; hydrogen; triethylamine at 120℃; Autoclave; | 81.5% |
1α-H, 2α-H, 4α-H, 5α-H-3,9-Dioxatricyclo<3.3.1.02,4>nonan-7-on
meta-hydroxybenzaldehyde
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol for 0.25h; Ambient temperature; ice-cooling (adding); | 72% |
With lithium diisopropyl amide | 57% |
Sodium; hydroxy-(3-hydroxy-phenyl)-methanesulfonate
meta-hydroxybenzaldehyde
Conditions | Yield |
---|---|
With ammonium acetate for 0.0333333h; microwave irradiation; | 72% |
salicylaldoxime
meta-hydroxybenzaldehyde
Conditions | Yield |
---|---|
With aluminum oxide; ammonium chlorochromate at 35℃; for 2h; oxidative deoximation; | 70% |
(R,S)3-hydroxymandelic acid
meta-hydroxybenzaldehyde
Conditions | Yield |
---|---|
With Ag-Ag2S nanoparticles supported on cellulose In water at 80℃; for 0.05h; Microwave irradiation; Green chemistry; | 65% |
Conditions | Yield |
---|---|
Stage #1: 3-Bromophenol With n-butyllithium; isopropylmagnesium chloride In tetrahydrofuran; hexane at 0 - 5℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at 0℃; for 1h; Further stages.; | 64% |
acetic anhydride
meta-hydroxybenzaldehyde
3-Acetoxy-1-(diacetoxymethyl)benzene
Conditions | Yield |
---|---|
With sulphated zirconia regioselective reaction; | 100% |
In neat (no solvent) at 20℃; for 0.1h; Green chemistry; chemoselective reaction; | 97% |
H6P2W18O62 at 20℃; for 0.5h; | 95% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 18h; Heating; | 100% |
With potassium carbonate; sodium iodide In ethanol for 3h; Reflux; | 100% |
With potassium carbonate In ethanol for 3h; Reflux; | 100% |
Conditions | Yield |
---|---|
In ethanol at 0 - 5℃; for 2h; | 100% |
at 20℃; for 12h; | 100% |
With benzene zuletzt unter Abdestillieren des gebildeten Wassers; |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 70℃; | 90% |
In acetone | 88% |
Conditions | Yield |
---|---|
With N-methylpyrrolidine zinc borohydride In tetrahydrofuran at 20℃; for 0.25h; | 100% |
With sodium tetrahydroborate In ethanol at 0℃; for 1h; Inert atmosphere; | 100% |
With sodium tetrahydroborate In ethanol at 0℃; for 1h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With bromine In dichloromethane | 100% |
With bromine In dichloromethane | 100% |
With 1,3-di-n-butyl-1H-imidazol-3-ium tribromide at 20℃; for 0.133333h; Neat (no solvent); regioselective reaction; | 95% |
3,5-dimethyl-4-nitroisoxazole
meta-hydroxybenzaldehyde
3-[(E)-2-(3-Methyl-4-nitro-isoxazol-5-yl)-vinyl]-phenol
Conditions | Yield |
---|---|
With pyrrolidine In neat (no solvent) at 20℃; for 0.116667h; Aldol Condensation; | 100% |
With base |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 12h; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 23℃; for 3h; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 14h; | 99% |
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol Heating; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 160℃; for 0.5h; | 90% |
Conditions | Yield |
---|---|
In di-isopropyl ether; water for 0.0416667h; Product distribution; Ambient temperature; separation of aldehyde; | 100% |
meta-hydroxybenzaldehyde
Sodium; hydroxy-(3-hydroxy-phenyl)-methanesulfonate
Conditions | Yield |
---|---|
With sodium hydrogensulfite In di-isopropyl ether; water for 0.0833333h; Product distribution; Ambient temperature; separation of aldehyde; | 100% |
With sodium hydrogensulfite at 50℃; for 1h; |
tert-butyldimethylsilyl chloride
meta-hydroxybenzaldehyde
3-(tert-butyl-dimethyl-sylanyloxy)benzaldehyde
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 25℃; for 16h; | 100% |
With triethylamine In dichloromethane at 20℃; for 2h; | 100% |
With 1H-imidazole In dichloromethane at 0 - 20℃; | 100% |
ethyl bromoacetate
meta-hydroxybenzaldehyde
ethyl 2-(3-formylphenoxy)acetate
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In acetone Heating; | 100% |
With potassium carbonate In acetonitrile at 70℃; for 4h; Inert atmosphere; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 20 - 80℃; for 3h; | 100% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide; toluene at 25℃; for 16h; | 100% |
With 18-crown-6 ether; potassium carbonate In acetonitrile Inert atmosphere; Reflux; | 99% |
With tetrabutylammomium bromide; potassium carbonate In tetrahydrofuran; water at 50℃; for 4h; | 94% |
meta-hydroxybenzaldehyde
4-piperidyl N-(2-biphenyl)carbamate
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride In dichloromethane for 3h; Ambient temperature; | 100% |
meta-hydroxybenzaldehyde
N-hexyl-2-cyanoacetylamide
Conditions | Yield |
---|---|
piperidine at 20℃; Knoevenagel condensation; solvent free; | 100% |
With piperidine In ethanol for 2h; Heating; | 57% |
meta-hydroxybenzaldehyde
1-bromo-3-propanol
3-(3-hydroxy-propoxy)-benzaldehyde
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 20℃; for 3h; Reflux; | 100% |
Stage #1: meta-hydroxybenzaldehyde With potassium carbonate In DMF (N,N-dimethyl-formamide) for 0.166667h; Stage #2: 1-bromo-3-propanol In DMF (N,N-dimethyl-formamide) for 2h; Heating / reflux; | 95% |
With potassium carbonate In acetonitrile for 48h; Heating; | 90% |
With potassium carbonate In acetonitrile for 48h; Heating / reflux; | 90% |
With potassium carbonate In acetonitrile for 5h; Heating / reflux; |
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In DMF (N,N-dimethyl-formamide) at 90℃; | 100% |
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 3h; |
Conditions | Yield |
---|---|
With sodium acetate; acetic acid In toluene for 4h; Reflux; Dean-Stark; | 100% |
In isopropyl alcohol at 80 - 90℃; for 2h; | 75% |
With piperidine; acetic acid for 0.333333h; Knoevenagel Condensation; Microwave irradiation; |
Conditions | Yield |
---|---|
at 20℃; for 12h; | 100% |
meta-hydroxybenzaldehyde
3(S)-(tert-butoxycarbonylamino)pyrrolidine
tert-butyl N-[(3S)-1-[(3-hydroxyphenyl)methyl]pyrrolidin-3-yl]carbamate
Conditions | Yield |
---|---|
Stage #1: meta-hydroxybenzaldehyde; 3(S)-(tert-butoxycarbonylamino)pyrrolidine With acetic acid In dichloromethane at 20℃; for 1h; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 4h; | 100% |
With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 24h; Inert atmosphere; | 89% |
Conditions | Yield |
---|---|
With pyridine; copper(I) bromide dimethylsulfide complex; sodium carbonate In acetonitrile at 75℃; for 48h; Inert atmosphere; solid phase reaction; | 100% |
N-benzyl-2-amino-5-(pyrrolidin-1-yl)benzamide
meta-hydroxybenzaldehyde
2-(3-hydroxyphenyl)-3-benzyl-6-(pyrrolidin-1-yl)-1,2,3,4-tetrahydro-1H-quinazolin-4-one
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In N,N-dimethyl acetamide at 20℃; for 2h; | 100% |
meta-hydroxybenzaldehyde
N-(3-hydroxy-benzylidene)-N'-(7-morpholin-4-yl-2-phenyl-pyrazolo[1,5-a]pyrimidin-5-yl)-hydrazine
Conditions | Yield |
---|---|
Stage #1: (7-morpholin-4-yl-2-phenyl-pyrazolo[1,5-a]pyrimidin-5-yl)hydrazine trifluoroacetate; meta-hydroxybenzaldehyde In ethanol at 1 - 30℃; for 1h; Stage #2: With NH-silica gel In methanol; dichloromethane | 100% |
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 0.5h; | 100% |
Conditions | Yield |
---|---|
Stage #1: meta-hydroxybenzaldehyde; aniline With acetic acid In dichloromethane at 20℃; for 24h; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 24h; | 100% |
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; silver trifluoromethanesulfonate In dichloromethane at 20℃; for 1h; | 92% |
Stage #1: meta-hydroxybenzaldehyde; aniline In ethanol at 80℃; for 3h; Inert atmosphere; Stage #2: With methanol; sodium tetrahydroborate for 1h; | 36% |
With sodium tris(acetoxy)borohydride; acetic acid In methanol at 20℃; for 42h; Reagent/catalyst; Time; |
Conditions | Yield |
---|---|
With copper(II) choride dihydrate; ammonium acetate In ethanol for 4h; Reflux; | 100% |
With 1,1,1,3',3',3'-hexafluoro-propanol; ammonium acetate at 55℃; for 1.5h; | 85% |
meta-hydroxybenzaldehyde
3,4-dichlorobenzyl bromide
3-[(3,4-dichlorobenzyl)oxy]benzaldehyde
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere; | 100% |
1. | sce-hmn:lyms 1 mmol/L | MUREAV Mutation Research. 206 (1988),17. |
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