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[ CAS No. 56441-55-5 ]

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Chemical Structure| 56441-55-5
Chemical Structure| 56441-55-5
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CAS No. :56441-55-5 MDL No. :MFCD00174341
Formula : C16H16O3 Boiling Point : 385.6?°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :256.30 g/mol Pubchem ID :-
Synonyms :

Safety of [ 56441-55-5 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338+P310 UN#:1759
Hazard Statements:H318 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 56441-55-5 ]

  • Downstream synthetic route of [ 56441-55-5 ]

[ 56441-55-5 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 56441-55-5 ]
  • [ 1486-51-7 ]
YieldReaction ConditionsOperation in experiment
93% With potassium hydroxide In ethanol for 4h; Heating;
90% With lithium hydroxide monohydrate; sodium hydroxide In ethanol for 17h; Reflux;
With potassium hydroxide
With potassium hydroxide
With sodium hydroxide
With hydroxide
With lithium hydroxide monohydrate
With potassium hydroxide In methanol; lithium hydroxide monohydrate; ethyl acetate 1 4-Benzyloxybenzoic acid (12) 4-Benzyloxybenzoic acid (12) To the solution of 0.5 g KOH in 40 ml MeOH, was added 6.5 mmol of ethyl 4-benzyloxybenzoate. After the resulting mixture was refluxed for 4 hrs, the excess methanol was removed. The residue was mixed with 30 ml water and extracted with ether twice. The water solution was acidified with conc. HCl and extracted with ethyl acetate. The ethyl acetate solution was washed with brine and dried. After evaporation of solvent, pure product was obtained in quantitative yield.
With sodium hydroxide In tetrahydrofuran; ethanol; lithium hydroxide monohydrate
With sodium hydroxide In methanol; lithium hydroxide monohydrate at 20℃; 5.2. 5-phenylisoxazole-3-carboxylic acid (AM1) General procedure: Diethyl oxalate (72.40 mmol, 10.60 g) was added to the freshlyprepared sodium ethylate solution (2.26 mol/mL, 80 mL) at 0 C andthen a solution of acetophenone (36.2 mmol, 4.35 g) in EtOH wasadded slowly. The reaction was allowed to warm to room temperatureand stirred for 8 h. The reaction was acidified with 3 mol/LHCl until the product precipitated. The precipitate was filtered anddried to afford intermediate 8.Hydroxylamine hydrochloride (54.30 mmol, 3.77 g) was addedto a solution of intermediate 8 (36.20 mmol, 7.97 g) in EtOH, andthe reaction was stirred at reflux condition. When the reaction wascomplete, the organic solvent was removed under reduced pressureand the residues were dissolved in water. The mixture wasextracted with ethyl acetate three times and the combined extractwas dried, concentrated and purified to afford intermediate 9.To a solution of intermediate 9 (10.0 mmol, 2.17 g) in MeOH(50 mL), NaOH (2 mol/L, 20 mL)was added. The reactionwas stirredat room temperature and monitored by TLC. The organic solventwas removed in vacuo and the residues were dissolved inwater. Themixture was acidified with 2 mol/L HCl until the product precipitated.The precipitate was filtered and dried to afford intermediateAM1.

Reference: [1]Lam, Jacky W.Y.; Dong, Yuping; Cheuk, Kevin K.L.; Tang, Ben Zhong [Macromolecules, 2003, vol. 36, # 21, p. 7927 - 7938]
[2]Pradhan, Balaram; Chakraborty, Nirmalangshu; Gupta, Ravindra Kumar; Shanker; Achalkumar, Ammathnadu S. [New Journal of Chemistry, 2017, vol. 41, # 2, p. 879 - 888]
[3]Tseng [Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1935, vol. 55, p. 132,141; engl. Ref. S. 30, 35][Chem.Abstr., 1935, p. 7981]
[4]Current Patent Assignee: BAYER AG - DE407669, 1924, C [Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 14, p. 1371][Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 14, p. 1371]
[5]Baggaley; Fears; Hindley; Morgan; Murrell; Thorne [Journal of Medicinal Chemistry, 1977, vol. 20, # 11, p. 1388 - 1393]
[6]Kasthuraiah [Journal of Materials Chemistry, 1996, vol. 6, # 10, p. 1619 - 1625]
[7]Shubashree; Sadashiva; Dhara, Surajit [Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 2002, vol. 381, p. 21 - 32]
[8]Current Patent Assignee: CITIZEN WATCH CO LTD - US2003/17278, 2003, A1
[9]Sleebs, Brad E.; Jarman, Kate E.; Frolich, Sonja; Wong, Wilson; Healer, Julie; Dai, Weiwen; Lucet, Isabelle S.; Wilson, Danny W.; Cowman, Alan F. [International Journal for Parasitology: Drugs and Drug Resistance, 2020, vol. 14, p. 188 - 200]
[10]Cheng, Maosheng; Su, Xin; Sun, Nannan; Sun, Yin; Tian, Linfeng; Yin, Wenbo; Zhang, Chu; Zhao, Dongmei; Zhao, Liyu; Zhao, Shizhen; Zheng, Yang [European Journal of Medicinal Chemistry, 2022, vol. 228]
  • 2
  • [ 56441-55-5 ]
  • [ 128958-65-6 ]
YieldReaction ConditionsOperation in experiment
74% With hydrazine hydrate In propan-1-ol for 48h; Heating;
With hydrazine hydrate In methanol for 6h; Heating;
With hydrazine hydrate In ethanol for 72h; Reflux;
With hydrazine hydrate
With hydrazine hydrate
With hydrazine hydrate In ethanol for 6h; Reflux; Synthesis of 4-alkoxy Benzoyl Hydrazine (3a-3u) 4-Alkoxy benzoic acid ethyl ester (12.7 mmol) and 20mL of ethanol were dissolved in 100 mL reaction flask andstirred at room temperature. Hydrazine hydrate (1.27 g, 25.4mmol) was added drop-wise to the mixture. The mixture washeated under reflux for 6 h. The solvent was evaporated underreduced pressure after the reaction completed to give the residue, which was washed with 100 mL water to obtain awhite solid (3a-3u).
With hydrazine hydrate In neat (no solvent) at 120℃; Sealed tube;
With hydrazine hydrate In neat (no solvent) at 120℃; Sealed tube; - Route B (R1 = aryl) General procedure: Note: hydrazine and carbon disulphide used during this procedure have to be handled withcaution.The carboxylic compound was first converted into its ethyl ester by refluxing in absoluteethanol in the presence of a few drops of H2SO4. The ester was then treated overnight withhydrazine hydrate (2 to 4 equiv.) without solvent at 120 °C. Evaporation of excess hydrazineyielded the corresponding hydrazide compound. The hydrazide, solubilized in absolute ethanol,was treated with CS2 (5 equiv.) in the presence of KOH (1.7 equiv.) at 85 °C for 3 h. Water wasadded and pH was adjusted to 2-3 with 1N HCl. The formed precipitate was collected byfiltration and washed with water, yielding the 1,3,4-oxadiazol-thione, which was used withoutfurther purification. Finally, the preceding compound was treated with hydrazine hydrate (10equiv.) in absolute ethanol at 100 °C overnight in a sealed tube. After evaporation of excesshydrazine, the residue was purified on a silica gel column to yield the final compound.
With hydrazine hydrate In ethanol at 100℃; Sealed tube; General procedure: The ester was then solubilized in EtOH and treated with hydrazine, hydrate (5 equiv.). The mixture was refluxed overnight and solvents were evaporated. Diethyl ether was added and the formed precipitate was filtered and washed with the same solvent to yield the expected hydrazide compound as a powder.
With hydrazine hydrate In ethanol at 100℃; Sealed tube; - General synthetic procedure for the preparation of hydrazides R1-CO-NHNH2 General procedure: To a solution of the acid R1-CO2H in EtOH was added concentrated H2SO4 (2 equiv.) and thereaction mixture was refluxed for 5h. After cooling to room temperature, water was added andthe solution was neutralized with Na2CO3. The aqueous phase was extracted twice with EtOAc.The organic phases were combined, dried over MgSO4, filtered and evaporated under vacuumto yield the ethyl ester, which was used without necessity of purification. The ester was then solubilized in EtOH and treated with hydrazine, hydrate (5 equiv.). Themixture was refluxed overnight and solvents were evaporated. Diethyl ether was added and the formed precipitate was filtered and washed with the same solvent to yield the expectedhydrazide compound as a powder.

Reference: [1]Mazouz; Gueddari; Burstein; Mansuy; Milcent [Journal of Medicinal Chemistry, 1993, vol. 36, # 9, p. 1157 - 1167]
[2]Li, Yan; Liu, Jie; Zhang, Hongquan; Yang, Xiangping; Liu, Zhaojie [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 8, p. 2278 - 2282]
[3]Location in patent: scheme or table El Bakali, Jamal; Klupsch, Frederique; Guedin, Aurore; Brassart, Bertrand; Fontaine, Gaelle; Farce, Amaury; Roussel, Pascal; Houssin, Raymond; Bernier, Jean-Luc; Chavatte, Philippe; Mergny, Jean-Louis; Riou, Jean-Francois; Henichart, Jean-Pierre [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 13, p. 3434 - 3438]
[4]Location in patent: scheme or table Ghani, Usman; Ullah, Nisar [Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 11, p. 4042 - 4048]
[5]Location in patent: scheme or table Hu, Lang-Xi; Li, De-Jiang [Heterocyclic Communications, 2010, vol. 16, # 2-3, p. 73 - 77]
[6]Zhu, Zi-Shi; Wang, Shi-Ben; Deng, Xian-Qing; Liu, Da-Chuan; Quan, Zhe-Shan [Letters in drug design and discovery, 2014, vol. 11, # 5, p. 628 - 635]
[7]Sevaille, Laurent; Gavara, Laurent; Bebrone, Carine; De Luca, Filomena; Nauton, Lionel; Achard, Maud; Mercuri, Paola; Tanfoni, Silvia; Borgianni, Luisa; Guyon, Carole; Lonjon, Pauline; Turan-Zitouni, Gülhan; Dzieciolowski, Julia; Becker, Katja; Bénard, Lionel; Condon, Ciaran; Maillard, Ludovic; Martinez, Jean; Frère, Jean-Marie; Dideberg, Otto; Galleni, Moreno; Docquier, Jean-Denis; Hernandez, Jean-François [ChemMedChem, 2017, vol. 12, # 12, p. 972 - 985]
[8]Baud, Damien; Bebrone, Carine; Becker, Katja; Benvenuti, Manuela; Cerboni, Giulia; Chelini, Giulia; Cutolo, Giuliano; De Luca, Filomena; Docquier, Jean-Denis; Feller, Georges; Fischer, Marina; Galleni, Moreno; Gavara, Laurent; Gresh, Nohad; Kwapien, Karolina; Legru, Alice; Mangani, Stefano; Mercuri, Paola; Pozzi, Cecilia; Sannio, Filomena; Sevaille, Laurent; Tanfoni, Silvia; Verdirosa, Federica; Berthomieu, Dorothée; Bestgen, Benoît; Frère, Jean-Marie; Hernandez, Jean-François [European Journal of Medicinal Chemistry, 2020, vol. 208]
[9]Gavara, Laurent; Legru, Alice; Verdirosa, Federica; Sevaille, Laurent; Nauton, Lionel; Corsica, Giuseppina; Mercuri, Paola Sandra; Sannio, Filomena; Feller, Georges; Coulon, Rémi; De Luca, Filomena; Cerboni, Giulia; Tanfoni, Silvia; Chelini, Giulia; Galleni, Moreno; Docquier, Jean-Denis; Hernandez, Jean-François [Bioorganic Chemistry, 2021, vol. 113]
[10]Legru, Alice; Verdirosa, Federica; Hernandez, Jean-François; Tassone, Giusy; Sannio, Filomena; Benvenuti, Manuela; Conde, Pierre-Alexis; Bossis, Guillaume; Thomas, Caitlyn A.; Crowder, Michael W.; Dillenberger, Melissa; Becker, Katja; Pozzi, Cecilia; Mangani, Stefano; Docquier, Jean-Denis; Gavara, Laurent [European Journal of Medicinal Chemistry, 2021, vol. 226]
  • 3
  • [ 120-47-8 ]
  • [ 100-39-0 ]
  • [ 56441-55-5 ]
YieldReaction ConditionsOperation in experiment
100% With Cs2CO3 In N,N-dimethyl-formamide 1 Ethyl 4-benzyloxybenzoate (11) Ethyl 4-benzyloxybenzoate (11) 35 mmol of benzyl bromide (BzBn, 35 mmol of ethyl 4-hydroxybenzoate (10), 14 g of Cs2CO3 and 40 ml of DMF were combined and stirred at RT ove night. Then the reaction mixture was poured into water and the product was collected by extraction. The organic solution was washed with brine and dried over MgSO4. After evaporation of solvent, pure product was obtained in yield of 100%.
98% With potassium carbonate at 100℃; for 6h;
98% With tri-n-octylmethylammonium chloride; potassium carbonate at 100℃; for 6h;
97% With potassium carbonate In propan-2-one at 20℃; for 48h;
95% With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 12h;
82% With potassium carbonate In propan-2-one for 3h; Heating;
78% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 16h;
75% With potassium carbonate In N,N-dimethyl-formamide at 70 - 80℃; Inert atmosphere;
With sodium hydride In N,N-dimethyl-formamide at 50℃;
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 20℃; 5.7. 4-(benzyloxy)benzoic acid (AM6) Intermediates 21 (11.0 mmol, 1.88 g), 22 (10.0 mmol, 1.66 g),K2CO3 (20.0 mmol, 2.76 g) and Catalytic amount KI were added toDMF (20 mL). The reaction was stirred at room temperature andmonitored by TLC. The reaction was poured in water and extractedwith ethyl acetate. Organic layer was dried over Na2SO4 andconcentrated to afford intermediate 23.Intermediate AM6 was prepared in a similar manner as that forintermediate AM1, using 23 instead of 9. 1H NMR (400 MHz, DMSO-d6) d 12.52 (s, 1H), 7.89 (d, J 8.9 Hz, 2H), 7.46 (d, J 7.0 Hz,2H), 7.40 (m, 2H), 7.35 (m, 1H), 7.10 (d, J 8.9 Hz, 2H), 5.18 (s, 2H).
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 20℃; 5.7. 4-(benzyloxy)benzoic acid (AM6) Intermediates 21 (11.0 mmol, 1.88 g), 22 (10.0 mmol, 1.66 g),K2CO3 (20.0 mmol, 2.76 g) and Catalytic amount KI were added toDMF (20 mL). The reaction was stirred at room temperature andmonitored by TLC. The reaction was poured in water and extractedwith ethyl acetate. Organic layer was dried over Na2SO4 andconcentrated to afford intermediate 23.Intermediate AM6 was prepared in a similar manner as that forintermediate AM1, using 23 instead of 9. 1H NMR (400 MHz, DMSO-d6) d 12.52 (s, 1H), 7.89 (d, J 8.9 Hz, 2H), 7.46 (d, J 7.0 Hz,2H), 7.40 (m, 2H), 7.35 (m, 1H), 7.10 (d, J 8.9 Hz, 2H), 5.18 (s, 2H).

Reference: [1]Current Patent Assignee: CITIZEN WATCH CO LTD - US2003/17278, 2003, A1
[2]Blanco; Bloch; Bugnet; Deloisy [Tetrahedron Letters, 2000, vol. 41, # 41, p. 7875 - 7878]
[3]Albert, Sébastien; Soret, Adrien; Blanco, Luis; Deloisy, Sandrine [Tetrahedron, 2007, vol. 63, # 13, p. 2888 - 2900]
[4]Lam, Jacky W.Y.; Dong, Yuping; Cheuk, Kevin K.L.; Tang, Ben Zhong [Macromolecules, 2003, vol. 36, # 21, p. 7927 - 7938]
[5]Location in patent: scheme or table El Bakali, Jamal; Klupsch, Frederique; Guedin, Aurore; Brassart, Bertrand; Fontaine, Gaelle; Farce, Amaury; Roussel, Pascal; Houssin, Raymond; Bernier, Jean-Luc; Chavatte, Philippe; Mergny, Jean-Louis; Riou, Jean-Francois; Henichart, Jean-Pierre [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 13, p. 3434 - 3438]
[6]Chandrasekhar; Jaya Prakash; Shyamsunder [Tetrahedron Letters, 2005, vol. 46, # 39, p. 6651 - 6653]
[7]San, Htet Htet; Wang, Shi-Jun; Jiang, Min; Tang, Xiang-Ying [Organic Letters, 2018, vol. 20, # 15, p. 4672 - 4676]
[8]Pradhan, Balaram; Chakraborty, Nirmalangshu; Gupta, Ravindra Kumar; Shanker; Achalkumar, Ammathnadu S. [New Journal of Chemistry, 2017, vol. 41, # 2, p. 879 - 888]
[9]Sleebs, Brad E.; Jarman, Kate E.; Frolich, Sonja; Wong, Wilson; Healer, Julie; Dai, Weiwen; Lucet, Isabelle S.; Wilson, Danny W.; Cowman, Alan F. [International Journal for Parasitology: Drugs and Drug Resistance, 2020, vol. 14, p. 188 - 200]
[10]Cheng, Maosheng; Su, Xin; Sun, Nannan; Sun, Yin; Tian, Linfeng; Yin, Wenbo; Zhang, Chu; Zhao, Dongmei; Zhao, Liyu; Zhao, Shizhen; Zheng, Yang [European Journal of Medicinal Chemistry, 2022, vol. 228]
[11]Cheng, Maosheng; Su, Xin; Sun, Nannan; Sun, Yin; Tian, Linfeng; Yin, Wenbo; Zhang, Chu; Zhao, Dongmei; Zhao, Liyu; Zhao, Shizhen; Zheng, Yang [European Journal of Medicinal Chemistry, 2022, vol. 228]
  • 4
  • [ 56441-55-5 ]
  • [ 120-47-8 ]
YieldReaction ConditionsOperation in experiment
99% With palladium diacetate; sodium hydride In N,N-dimethyl acetamide at 50℃; for 5h; Inert atmosphere;
99% With palladium diacetate; sodium hydride In N,N-dimethyl acetamide at 50℃; for 5h; Inert atmosphere; 20 Under the protection of nitrogen, palladium acetate (3.4 mg, 0 . 015 mmol, 5 mol %) and sodium hydride (60% in oil, 18 mg, 0.45 mmol, 1.5 equiv) suspension for DMA (1.0 ml), 25 °C stirring 5 minutes, adding compound 19 (0.3 mmol) in DMA (0.5 ml) solution, then in 50 °C reaction 5 hours, adding ice water stopped reaction, dilute hydrochloric acid for adjusting the pH value to 3.5, extracted with ethyl acetate, the combined extract, sulfate to dry, dry [...], column chromatography purification, to obtain the product 20, yield 99%.
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