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Chemical Structure| 725-14-4 Chemical Structure| 725-14-4

Structure of 725-14-4

Chemical Structure| 725-14-4

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Product Details of [ 725-14-4 ]

CAS No. :725-14-4
Formula : C14H12O3
M.W : 228.24
SMILES Code : O=C(O)C1=CC=C(C=C1)C2=CC=C(C=C2)OC
MDL No. :MFCD00185792
Boiling Point : No data available
InChI Key :FDPKGXQCDURRBM-UHFFFAOYSA-N
Pubchem ID :2759552

Safety of [ 725-14-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 725-14-4 ]

* 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 [ 725-14-4 ]

[ 725-14-4 ] Synthesis Path-Downstream   1~35

  • 2
  • [ 123-51-3 ]
  • [ 725-14-4 ]
  • [ 49708-80-7 ]
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  • [ 725-14-4 ]
  • [ 68294-33-7 ]
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  • [ 725-14-4 ]
  • [ 67132-14-3 ]
YieldReaction ConditionsOperation in experiment
99.8% With thionyl chloride; at 50℃; for 3h; 2.4.c <strong>[725-14-4]4'-methoxy-biphenyl-4-carboxylic acid</strong> chloride A solution of 3.0 g (0.013 mol) of <strong>[725-14-4]4'-methoxy-biphenyl-4-carboxylic acid</strong> in 47.4 mL (0.65 mol) of thionyl chloride is stirred at 50 C. for three hours. After removal of thionyl chloride using the rotary evaporator the product is obtained as a yellowish solid, which is stored in the refrigerator. Yield: 3.2 g (99.8% of theory); C15H14O2 (M=246.696); calc.: molar peak (M+H)+: 246/248 fnd.: molar peak (M+H)+: 246/248.
With thionyl chloride; (b) 4-Acetylphenyl 4'-methoxybiphenyl-4-carboxylate (8b).; 4'-Methoxybiphenyl-4-carboxylic acid (400 mg, 1.60 mmol) was dissolved in thionyl chloride (25 rnL) and allowed to stir overnight. The thionyl chloride was then removed under reduced pressure and the acid chloride was carried on crude. The acid chloride was dissolved in dichloromethane and 4-hydroxyacetophenone (218 mg, 1.60 mmol) was added to the solution. Sodium hydride (60% in mineral oil, 64 mg, 1.60 mmol) was then added slowly to the reaction and allowed to stir for 5h. The reaction was then quenched with saturated aqueous sodium bicarbonate and the solution was extracted twice with dichloromethane. The combined organic layers were then dried over magnesium sulfate, filtered and evaporated under reduced pressure to a solid which was carried on crude. 1HNMR (DMSO): δ 8.18 (d, J=5.1 Hz, 2H), 8.08 (d, J=5.1 Hz, 2H), 7.88 (d, J=5.1 Hz, 2H), 7.76 (d, J=5.1 Hz, 2H), 7.48 (d, J=5.1 Hz, 2H), 7.08 (d, J=5.1 Hz, 2H), 3.82 (s, 3H), 2.62 (s, 3H).
  • 10
  • [ 13021-18-6 ]
  • [ 725-14-4 ]
YieldReaction ConditionsOperation in experiment
100% With sodium hydroxide; bromine; In 1,4-dioxane; water; at 0℃; for 3h; 2.4.b 4'-methoxy-biphenyl-4-carboxylic acid 6.0 mL (117 mmol) of bromine is slowly added dropwise to a solution of 15.6 g (390.9 mmol) of NaOH in 70 mL water at 0 C. Then 8.8 g (39.1 mmol) of 1-(4'-methoxy-biphenyl-4-yl)-ethanone in 50 mL dioxane is slowly added. After three hours the solid formed is filtered off, taken up in dichloromethane and filtered again. The filtrate is freed from solvent using the rotary evaporator. Yield: 9.0 g (100.0% of theory); C15H14O2 (M=228.250); calc.: molar peak (M-H)-: 227 fnd.: molar peak (M-H)-: 227.
In 1,4-dioxane; A solution of 18 g of 4-acetyl-4'-methoxybiphenyl in 285 ml of dioxane was oxidized with a dilute sodium hypobromite. Recrystallization from ethanol and acetic acid gave 4'-methoxybiphenyl-4-carboxylic acid melting at 285 C.
In 1,4-dioxane; 18 g of 4-acetyl-4'-methoxybiphenyl was dissolved in 285 ml of dioxane and oxidized with a dilute sodium hypobromite. The product was recrystallized in a mixture of ethanol and acetic acid to obtain 4'-methoxybiphenyl-4-carboxylic acid.
  • 12
  • [ 729-17-9 ]
  • [ 725-14-4 ]
YieldReaction ConditionsOperation in experiment
98% [0158] Step 2 : 4 -METHOXY-BIPHENYL-4-CARBOXYLIC acid. 1 N NAOH (148.5 mL, 148. 5 mmol) was added under nitrogen to a solution of 4 -METHOXY-BIPHENYL-4-CARBOXYLIC acid methyl ester (12. 0G, 49.5 mmol), prepared in the previous step, in 1 L of THF plus 250 ML of water at room temperature. After the addition the reaction was refluxed for 16.5 h (overnight). After cooling to approximately room temperature the reaction was acidified by the addition of 1 N HC1 and then concentrated under reduced pressure. The solid that formed was collected by filtration and dried under reduced pressure to give 4 -METHOXY-BIPHENYL-4-CARBOXYLIC acid (11. 11 G, 98%) as a white solid, mp 245-250C ; MS (ESI) M/Z 227 [M-H]-. Elemental Analysis for C14H1203 : Calc'd: C, 73.67 ; H, 5.30 ; N, 0.00 ; Found: C, 69.52 ; H, 5.01 ; N, 0.04.
  • 13
  • [ 586-76-5 ]
  • [ 5720-07-0 ]
  • [ 725-14-4 ]
YieldReaction ConditionsOperation in experiment
99% With potassium carbonate; palladium dichloride; In PEG400; water; at 20℃; for 0.133333h;Air atmosphere; General procedure: A mixture of arylboronic acid (0.5 mmol), aryl bromides/iodides (0.6 mmol), PdCl2 (0.0025 mmol), K2CO3 (1.75 mmol), PEG400 1.5 mL, and H2O 1.5 mL were added to a 50 mL round-flask, and stirred at room temperature for the desired time until complete consumption of starting material as judged by TLC. Then, the reaction mixture was extracted with ether (10 mL×4) and the combined organic layers were dried over anhydrous MgSO4 (acidification was needed for carboxyl substituted substrates before extraction). The solvent was removed by evaporation under reduced pressure to afford the crude products, which were further purified by column chromatography on silica gel using petroleum ether and ethyl acetate as the eluent.
98% With potassium carbonate; In water; at 20℃; for 4h;Green chemistry; General procedure: A 50 mL flask was charged with an aryl halide (1.0 mmol), anaryl boronic acid (1.2 mmol), K2CO3 (2.0 mmol), nanocatalyst(0.05 mol% Pd) and deionized water (5 mL). The reactionwas stirred at room temperature for 4 h. The progress ofthe reaction was monitored by thin-layer chromatography After the reaction was completed, distilled water (25 mL) wasadded to the mixture and dilute 2 mol/L HCl was added dropwiseto pH 3.0-4.0 with stirring, and the mixture was heatedto 100 C for 10 min. The white solid that had formed wasfiltered off and washed with hot water. After drying, it wasdissolved in ether (5 mL) and was rapidly separated using asilica gel column. Elution with ether left behind small amountsof impurities and traces of palladium black to give a crudeproduct. The ether solution was evaporated to 3-5 mL andrecrystallized to obtain a pure product. All the products 3a-uare known compounds and were characterized by comparingtheir melting points and 1H NMR spectra with those preparedrecently by using a water-soluble glycine-based Pd catalyst,PdCl2(NH2CH2CO2H)2.10 The melting points and 1H NMRdata of 3a-u are listed in the supplemental material.
  • 14
  • [ 586-76-5 ]
  • [ 13139-86-1 ]
  • [ 725-14-4 ]
  • 16
  • [ 129182-18-9 ]
  • Wang-resin-CH2O-(p-C6H4)-CH2OC(O)(p-C6H4)-I [ No CAS ]
  • [ 725-14-4 ]
  • 17
  • [ 350792-90-4 ]
  • Wang-resin-CH2O-(p-C6H4)-CH2OC(O)(p-C6H4)-I [ No CAS ]
  • [ 725-14-4 ]
  • 18
  • [ 130952-94-2 ]
  • Wang resin-tethered 4-iodobenzoic acid [ No CAS ]
  • [ 725-14-4 ]
  • 19
  • [ 350792-90-4 ]
  • Wang resin-tethered 4-iodobenzoic acid [ No CAS ]
  • [ 725-14-4 ]
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  • [ 725-14-4 ]
  • [ 6232-11-7 ]
  • [ 742106-41-8 ]
  • 21
  • [ 619-58-9 ]
  • [ 5720-07-0 ]
  • [ 725-14-4 ]
YieldReaction ConditionsOperation in experiment
95% With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 80℃; for 6h;Inert atmosphere; Method B.A solution of 4-methoxyphenyl boronic acid (1 g, 6.58 mmol), 4-iodobenzoic acid (1.63 g, 6.58 mmol) and cesium carbonate (5.36 g, 16.45 mmol) in 3:1 1,2- dimethoxyethane/water was deoxygenated with nitrogen for 15 minutes. Pd(PPtLs)4 (380 mg, 0.329 mmol) was then added and the solution was heated to 80 C for 6h. The reaction was allowed to cool and acidified with 2M HCl which caused a precipitate to form. The precipitate was filtered and the filtrate was extracted twice with dichloromethane. The organic layer was then dried over magnesium sulfate, filtered through diatomaceous earth filter aid (CELITE) and evaporated under reduced pressure to yield a combined 1.5O g (95%). 1HNMR (DMSO): δ 7.99 (d, J=8.4 Hz, 2H), 7.74 (d, J=8.4 Hz, 2H), 7.69 (d, J=8.7 Hz, 2H), 7.04 (d, J=8.7 Hz, 2H), 3.80 (s, 3H). 13CNMR (DMSO): δ 167.17, 159.49, 143.90, 131.16, 129.91, 128.77, 128.09, 126.08, 114.45, 55.17.
89% With Pd/C; potassium carbonate; In water; at 110℃; for 1h; General procedure: The Ni and Pd carbon aerogels were always sinked in water 24 h before their use as catalysts and kept in the same solvent.Catalytic reactions: In a 100 mL three necked round-bottom flask, arylboronic acid (15 mmol), aryl halide (10 mmol) and K2CO3 (2.76 g, 20 mmol) were dissolved in 20 mL of H2O. Then, Ni or Pd carbon aerogel (0.1 mmol, 1 mol %) was added to the mixture and the reaction was carried out under reflux (110 C), in the presence of air and mechanical stirring. Periodic sampling of the reaction media was made to analyze the reaction evolution by GC and 1H NMR measurements. The liquid phase was decanted and the carbon aerogel was washed with water. This water extracts and the reactive solution were mixed together and acidified until pH 1 to cause the precipitation of the final product. The solid was filtrated, washed with water and dried. The pieces of aerogel were washed with AcOEt, with water and were kept submerged in this solvent before reused.
  • 25
  • [ 725-14-4 ]
  • 3'-bromo-4'-methoxy-biphenyl-4-carboxylic acid 4-(4-methoxy-phenylazo)-phenyl ester [ No CAS ]
  • 26
  • [ 725-14-4 ]
  • 3'-bromo-4'-methoxy-biphenyl-4-carboxylic acid 4-(4-ethoxy-phenylazo)-phenyl ester [ No CAS ]
  • 27
  • [ 725-14-4 ]
  • 3'-bromo-4'-methoxy-biphenyl-4-carboxylic acid 4-(4-butoxy-phenylazo)-phenyl ester [ No CAS ]
  • 28
  • [ 725-14-4 ]
  • [ 742106-42-9 ]
  • 29
  • [ 725-14-4 ]
  • 4'-methoxy-biphenyl-4-carboxylic acid 4-hydroxycarbamoyl-benzylamide [ No CAS ]
  • 30
  • [ 725-14-4 ]
  • [ 742106-43-0 ]
  • 32
  • [ 350792-83-5 ]
  • [ 725-14-4 ]
  • 33
  • [ 725-14-4 ]
  • 4'-Undec-10-enyloxy-biphenyl-4-carboxylic acid 4-((R)-1-butoxycarbonyl-ethoxy)-phenyl ester [ No CAS ]
  • 34
  • [ 725-14-4 ]
  • 4'-Undec-10-enyloxy-biphenyl-4-carboxylic acid 4-((R)-1-butoxycarbonyl-ethoxy)-3-nitro-phenyl ester [ No CAS ]
  • 35
  • [ 725-14-4 ]
  • 4'-Undec-10-enyloxy-biphenyl-4-carboxylic acid 4-((R)-1-butoxycarbonyl-ethoxy)-2-nitro-phenyl ester [ No CAS ]
 

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