Conditions | Yield |
---|---|
With hydrogenchloride; acetic acid at 100℃; for 2h; | 90% |
With hydrogenchloride; water at 100℃; for 12h; | 88% |
With hydrogenchloride |
Conditions | Yield |
---|---|
Stage #1: carbon monoxide With C28H16N2O6Se In butan-1-ol under 750.075 Torr; for 2h; Reflux; Stage #2: p-Xylylene dichloride With tetrabutylammomium bromide; sodium hydroxide In butan-1-ol at 50℃; under 750.075 Torr; for 24h; | 90% |
Stage #1: carbon monoxide With C28H22CoN4O6 In butan-1-ol at 60℃; under 760.051 Torr; for 2h; Glovebox; High pressure; Green chemistry; Stage #2: p-Xylylene dichloride With tetra-(n-butyl)ammonium iodide; sodium hydroxide In butan-1-ol at 60℃; under 760.051 Torr; for 22h; Glovebox; High pressure; Green chemistry; regioselective reaction; | 80% |
1,4-bis(bromomethyl)benzene
carbon monoxide
1,4-phenylenediacetic acid
Conditions | Yield |
---|---|
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium iodide In formic acid at 90℃; under 760 Torr; for 18h; Carbonylation; | 89% |
1,4-bis(2,2-dibromoethenyl)benzene
1,4-phenylenediacetic acid
Conditions | Yield |
---|---|
Stage #1: 1,4-bis(2,2-dibromoethenyl)benzene With n-butyllithium In tetrahydrofuran at 0℃; for 1.5h; Stage #2: With 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran for 2h; | 60% |
diethyl 2,2'-(1,4-phenylene)diacetate
1,4-phenylenediacetic acid
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water for 9h; Heating; | 57% |
carbon monoxide
p-xylylene glycol
A
1,4-phenylenediacetic acid
B
4-tolylacetic acid
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); hydrogen iodide In acetone at 90℃; under 68400 Torr; for 42h; | A 48% B 16 % Spectr. |
carbon monoxide
p-xylylene glycol
A
para-xylene
B
1,4-phenylenediacetic acid
C
4-tolylacetic acid
Conditions | Yield |
---|---|
With hydrogen iodide; tetrakis(triphenylphosphine) palladium(0) In acetone at 90℃; under 68400 Torr; for 42h; Carbonylation; reduction; | A n/a B 48% C 16% |
octane
para-xylene
n-pentylsodium
A
1,4-phenylenediacetic acid
B
4-tolylacetic acid
C
hexanoic acid
Conditions | Yield |
---|---|
Behandlung des Reaktionsprodukts mit festem CO2; |
Conditions | Yield |
---|---|
With morpholine; sulfur Erwaermen des Reaktionsprodukts mit aethanol. Kalilauge; |
Conditions | Yield |
---|---|
With morpholine; sulfur Erwaermen des Reaktionsprodukts mit aethanol. Kalilauge; |
Conditions | Yield |
---|---|
With octane; n-pentylsodium anschliessendes Behandeln mit festem Kohlendioxid; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 87 percent / triethylene glycol / 1 h / 90 °C 2: 90 percent / conc. HCl; acetic acid / 2 h / 100 °C View Scheme | |
Multi-step reaction with 2 steps 1: aq. ethanol / Heating 2: aq. H2SO4 / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 78 percent / SnCl4 / CH2Cl2 / 24 h / Ambient temperature 2: 86 percent / Raney nickel / ethanol / 4 h / Heating 3: 57 percent / sodium hydroxide / ethanol; H2O / 9 h / Heating View Scheme |
diethyl α-methylthio-1,4-benzenediacetate
1,4-phenylenediacetic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 86 percent / Raney nickel / ethanol / 4 h / Heating 2: 57 percent / sodium hydroxide / ethanol; H2O / 9 h / Heating View Scheme |
diethyl 2,2'-(1,4-phenylene)diacetate
A
2-(4-(2-ethoxy-2-oxoethyl)phenyl)acetic acid
B
1,4-phenylenediacetic acid
Conditions | Yield |
---|---|
With lithium hydroxide monohydrate; water In tetrahydrofuran; ethanol |
Conditions | Yield |
---|---|
With sulfuric acid-d2 In dimethylsulfoxide-d6 |
Conditions | Yield |
---|---|
Stage #1: 1,4-diethynylbenzene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: With 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran for 2h; Stage #3: With oxone In acetone at 50℃; for 12h; | |
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 1.2: 2 h / -78 °C / Inert atmosphere 2.1: oxone||potassium monopersulfate triple salt; water / acetone / 12 h / 50 °C / Inert atmosphere View Scheme |
1,4-phenylenediacetic acid
Conditions | Yield |
---|---|
With oxone||potassium monopersulfate triple salt; water In acetone at 50℃; for 12h; Inert atmosphere; | 689 mg |
methanol
1,4-phenylenediacetic acid
(4-methoxycarbonylmethylphenyl)acetic acid methyl ester
Conditions | Yield |
---|---|
With sulfuric acid Reflux; | 100% |
With sulfuric acid at 80℃; for 94h; Inert atmosphere; | 90% |
With thionyl chloride for 4h; Reflux; | 85% |
ethanol
1,4-phenylenediacetic acid
(4-methoxycarbonylmethylphenyl)acetic acid methyl ester
Conditions | Yield |
---|---|
With sulfuric acid In water at 80℃; for 12h; Inert atmosphere; | 99% |
N(1),N(2)-bis(t-butyloxycarbonyl)-1,2,4-butanetriamine
1,4-phenylenediacetic acid
Conditions | Yield |
---|---|
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In acetonitrile at 0 - 20℃; Reflux; | 97% |
1,4-phenylenediacetic acid
phenylenediacetic acid-2,2,2',2'-d4
Conditions | Yield |
---|---|
With potassium hydroxide; water-d2 at 160℃; for 28h; | 95% |
1,4-phenylenediacetic acid
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 25℃; for 12h; | 94% |
1,2-bis(5-methylisoxazol-3-yl)hydrazine
1,4-phenylenediacetic acid
zinc(II) acetate dihydrate
Conditions | Yield |
---|---|
In water at 70 - 120℃; for 72.5h; | 93% |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran Ambient temperature; | 92% |
Stage #1: 1,4-phenylenediacetic acid With dimethyl sulfide borane In tetrahydrofuran for 18h; Stage #2: With hydrogenchloride In tetrahydrofuran; water | 87% |
With dimethylsulfide borane complex In tetrahydrofuran at 0 - 20℃; for 24h; Inert atmosphere; | 81.8% |
1,4-phenylenediacetic acid
4'-methoxy-N-(azulen-1-ylmethylene)aniline
Conditions | Yield |
---|---|
for 10h; Heating; | 91% |
Conditions | Yield |
---|---|
Stage #1: pyrrolidine; 1,4-phenylenediacetic acid With (dimethoxy)methylsilane; molybdenum hexacarbonyl at 65℃; Stage #2: trimethylsilyl cyanide In 2,2,2-trifluoroethanol at 20℃; for 1h; chemoselective reaction; | 91% |
ethanol
1,4-phenylenediacetic acid
diethyl 2,2'-(1,4-phenylene)diacetate
Conditions | Yield |
---|---|
With sulfuric acid for 15h; Reflux; | 90% |
With sulfuric acid at 80℃; | 87% |
With sulfuric acid for 18h; Heating; | 74% |
acetyl chloride for 18h; Heating / reflux; |
1,4-phenylenediacetic acid
1,4-benzenediacetaldehyde
Conditions | Yield |
---|---|
With triethylsilane; tris(pentafluorophenyl)borate In benzene at 23℃; for 6h; Schlenk technique; Inert atmosphere; | 90% |
Multi-step reaction with 3 steps 1: 74 percent / aq. H2SO4 / 18 h / Heating 2: 84 percent / LiAlH4 / diethyl ether / 3 h / Heating 3: 62 percent / Dess-Matin periodinane / CH2Cl2 / 4 h / 20 °C View Scheme |
1,4-phenylenediacetic acid
Conditions | Yield |
---|---|
In N,N-dimethyl acetamide; water High Pressure; mixt. of Eu(NO3)3*6H2O (0.4 mmol), H2pda (0.6 mmol), H2O and dimethylacetamide heated in Teflon-lined autoclave at 105°C for 2 d, cooled slowly to room temp.; elem. anal.; | 90% |
1,4-phenylenediacetic acid
Conditions | Yield |
---|---|
In ethanol; water at 180℃; for 1.16667h; | 90% |
1,4-phenylenediacetic acid
Conditions | Yield |
---|---|
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 23℃; for 18h; | 89% |
1,4-phenylenediacetic acid
phenylglyoxylic acid potassium salt
1,4-Phenylene bis(phenylmaleic anhydride)
Conditions | Yield |
---|---|
With acetic anhydride for 1h; Heating; | 88% |
Conditions | Yield |
---|---|
With sodium hydroxide at 120℃; for 72h; Sealed tube; Autoclave; | 88% |
1,4-phenylenediacetic acid
Diphenylphosphine oxide
(1,4-phenylenebis(methylene))bis(diphenylphosphine oxide)
Conditions | Yield |
---|---|
With sodium persulfate; silver carbonate In acetonitrile at 80℃; | 88% |
1,4-phenylenediacetic acid
1,4-benzenediacetyl dichloride
Conditions | Yield |
---|---|
With Vilsmeier reagent In toluene at 35 - 40℃; for 0.25h; | 87% |
With thionyl chloride | |
With phosphorus pentachloride |
1,4-phenylenediacetic acid
L-Leu-L-Pro-OMe
1,4-phenylenedi(acetyl-L-leucyl-L-proline methyl ester)
Conditions | Yield |
---|---|
Stage #1: 1,4-phenylenediacetic acid With diisopropyl-carbodiimide In dichloromethane for 0.75h; Stage #2: L-Leu-L-Pro-OMe In dichloromethane for 16h; | 86% |
1,4-phenylenediacetic acid
Conditions | Yield |
---|---|
In N,N-dimethyl acetamide; water High Pressure; mixt. of Gd(NO3)3*6H2O (0.4 mmol), H2pda (0.6 mmol), H2O and dimethylacetamide heated in Teflon-lined autoclave at 105°C for 2 d, cooled slowly to room temp.; elem. anal.; | 86% |
1,4-phenylenediacetic acid
Conditions | Yield |
---|---|
In water for 72h; Autoclave; High pressure; | 86% |
Conditions | Yield |
---|---|
With sodium carbonate In water High Pressure; addn. of aq. soln. of sodium carbonate to aq. soln. of carbon compd., addn. of aq. soln. of cobalt compd. at room temp., sealing in stainless steel reactor, heating at 120°C for 48 h; cooling, isolation of crystals by hand, washing with water, drying over filter paper, elem. anal.; | 85% |
1,4-phenylenediacetic acid
Conditions | Yield |
---|---|
In ethanol; water at 180℃; for 1.16667h; Milling; | 85% |
1,4-phenylenediacetic acid
Benzoylformic acid
1,4-Phenylene bis(phenylmaleic anhydride)
Conditions | Yield |
---|---|
With acetic anhydride; sodium hydride Reflux; | 85% |
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