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[ CAS No. 5438-19-7 ]

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Chemical Structure| 5438-19-7
Chemical Structure| 5438-19-7
Structure of 5438-19-7 * Storage: {[proInfo.prStorage]}

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Product Details of [ 5438-19-7 ]

CAS No. :5438-19-7 MDL No. :MFCD00013989
Formula : C10H12O3 Boiling Point : 304.9°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :180.20 g/mol Pubchem ID :138500
Synonyms :

Safety of [ 5438-19-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5438-19-7 ]

  • Downstream synthetic route of [ 5438-19-7 ]

[ 5438-19-7 ] Synthesis Path-Downstream   1~16

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  • [ 463-72-9 ]
  • [ 5438-19-7 ]
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  • [ 5438-19-7 ]
  • [ 40782-58-9 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride
With phosphorus pentachloride
With thionyl chloride In benzene for 3h; Heating;
With thionyl chloride for 2h; Heating;
With thionyl chloride; N,N-dimethyl-formamide In toluene at 60 - 70℃; for 0.5h;
With thionyl chloride for 2h; Heating;
With thionyl chloride
With thionyl chloride for 0.5h; Heating;
With thionyl chloride; N,N-dimethyl-formamide Heating;
With pyridine; thionyl chloride In toluene Heating;
With thionyl chloride In benzene
With thionyl chloride
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane for 10h;
With thionyl chloride at 90℃; for 4h;
With thionyl chloride In dichloromethane for 1h; Heating;
With thionyl chloride
With thionyl chloride Heating;
With thionyl chloride Reflux;
With thionyl chloride
With thionyl chloride
With thionyl chloride
With thionyl chloride Reflux;
With thionyl chloride
With thionyl chloride for 1h; Reflux;
With thionyl chloride for 3h; Reflux;
With thionyl chloride Reflux;
With thionyl chloride
With thionyl chloride Reflux;
With thionyl chloride
With thionyl chloride
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 0.5h; Inert atmosphere;
With phosphorus pentachloride In toluene for 4h; Heating;
With thionyl chloride Heating;
With thionyl chloride; N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere; Step A General procedure: To the corresponding benzoic acid (3.3 mmol), thionyl chloride (10 mL) and a catalytic quantity of DMF were slowly added under an argon atmosphere. The suspension was refluxed until all the solid dissolved (2 h). Excess SOCl2 was then removed under reduced pressure, and the solid residue was co-evaporated twice with anhydrous toluene (2 x 10 mL). Crude benzoic acid chloride was immediately re-dissolved in dry toluene (20 mL) and drawn into a syringe for use in the following step.
With thionyl chloride for 3h; Reflux;
With thionyl chloride at 40 - 50℃; for 2h; 4-{4'-[(E)-(4"-Propoxybenzoyl)oxyphenyl]diazenyl}-phthalonitrile (3c). A mixture of 0.3 g (0.002 mol) of 4-(4'-propoxy)benzoic acid and 0.6 mL (0.005 mol) of thionyl chloride was heated at 40-50° at stirring till the gas evolution ceased (about 2 h). 0.9 g (0.0036 mol) of compound 3b and 1 mL of pyridine were then added, and the reaction mixture was refluxed at 85°C during 2 h. The obtained mass was poured into water; the precipitate was filtered off, washed with water till neutral reaction of the washings, and dried. The product was extracted with chloroform and purified by column chromatography (M60 silica gel, chloroform as eluent). Yield 0.7 g (47%), mp 148°C. IR spectrum (KBr), ν, cm-1: 2924 s, 2852 (CH), 2235 s (C≡N), 1729 s (C=O), 1267 s (Ar-O-Alk), 1608 s (N=N). 1H NMR spectrum (CDCl3), δ, ppm: 8.28 s (1H, H1), 8.19 m (1H, H3), 7.97 m (2H, H4), 7.95 m (1H, H2), 7.49 m (2H, H5), 7.03 m (2H, H7), 6.22 m (2H, H8), 1.61 m (2H, H9), 0.90 m (3H, H10). Electronic absorption spectrum, λmax, nm: 380 (chloroform); 387 (DMF). Found, %: C 69.93; H 4.12; N 13.18. C24H18N4O3. Calculated, %: C 70.23; H 4.42; N 13.65.
With hydrogenchloride; thionyl chloride In water
With thionyl chloride In N,N-dimethyl-formamide at 80℃; for 3h; Inert atmosphere;
With thionyl chloride at 50℃; for 0.5h; 4 Example 4; (4-Propoxy-phenyl)-(2-(S)-pyrrolidin-l-ylmethyl-pyrrolidin-l-yl)-methanone; Procedure F: 4-Propoxybenzoic acid (180 mg, 1.00 mmol) is dissolved in 2.0 mL of thionyl chloride and stirred at 50 0C for 30 min. The excess thionyl chloride is removed in vacuo. The residue is dissolved in 1.0 mL of CH2Cl2. (S)(+)-l-(2- pyrrolidinylmethyl)pyrrolidine (164 mg, 1.07mmol) and triethylamine (108 mg, 1.07 mmol) are dissolved in 3.0 mL of CH2Cl2 and cooled to 0 °C. The acid chloride solution is added to this mixture and stirred at room temperature for 1 h. The reaction mixture is diluted with CH2Cl2, washed with brine, dried over Na2Sθ4, filtered and evaporated.The crude product is applied to silica-gel column chromatography (CH2Cl2: 2M NH3 in MeOH = 20: 1) to provide 298 mg (94%) of the titled compound. Observed Mass: 317(M+1).
With thionyl chloride for 3h; Reflux;
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0℃; for 1h; Inert atmosphere;
With thionyl chloride for 2h; Reflux;
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2h; Cooling with ice; 35 Example 35. Preparation of compound 35 with lappaconitine and 4-n-propoxybenzoic acid: Weigh 181mg of 4-n-propoxybenzoic acid in a 25ml dry round bottom flask, add 5ml of dry dichloromethane to dissolve, add a few drops of dimethylformamide, and add 381mg of oxalyl chloride in an ice bath. After reacting at room temperature for 2 hours, 4-n-propoxybenzoyl chloride was prepared. Weigh 89 mg of N-deacetyllappaconitine in a 25 ml round-bottom flask, and add 10 ml of dry dichloromethane to dissolve it. Add 105μl of dry pyridine under the protection of Ar gas, slowly add the prepared acid chloride dropwise to the substrate solution, and react at 35°C. The progress of the reaction is checked by thin-layer chromatography. The reaction is complete after 15 hours. Add a saturated aqueous sodium carbonate solution dropwise to the reaction solution to adjust the pH value of the reaction solution to 10. The reaction solution was extracted with dichloromethane, the dichloromethane layer was dried with anhydrous sodium sulfate, the sodium sulfate solid was filtered off, and the dichloromethane was spin-dried to obtain the crude product, which was separated and purified by column chromatography to obtain the target compound. Its structure and characteristics are as follows:
With thionyl chloride at 0℃; for 24h; Reflux; 8.1.2.2. Method B, synthesis of amide bond using thionyl chloride. General procedure: The appropriate carboxylic acid (1 eq.) was cooled to 0 C and then thionyl chloride (2 eq.) was added dropwise. The mixture was thenheated under reflux for 2 h, and the excess of thionyl chloride wasevaporated under vacuum. The acid chloride was dissolved in dryTHF and added dropwise to a solution of the appropriate amine (0.9eq.) and DIPEA (3 eq.) in THF. After completion, the reactionmixture was diluted with ethyl acetate and washed with a saturatedaqueous solution of ammonium chloride and brine. Theorganic layerwas dried over anhydrous sodium sulfate, filtered, andconcentrated in vacuo. The residue was purified using columnchromatography (chloroform/methanol as eluents). The yieldswere around 50-70%.

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  • 4
  • [ 115478-59-6 ]
  • [ 5438-19-7 ]
YieldReaction ConditionsOperation in experiment
98.9% Stage #1: methyl 4-propoxy benzoate With sodium hydroxide In methanol at 60 - 65℃; for 3h; Stage #2: With hydrogenchloride In methanol; water General procedure for hydrolysis General procedure: To the stirred solution of the ester was prepared above treated with sodium hydroxide (2.0 eq) in methanol at 60-65 °C for 3 h. Acidified the reaction mixture with hydrochloric acid and isolated the corresponding product in good yield and methanol was recovered.
With alkali
With potassium hydroxide In ethanol; water for 2h; Reflux; Synthesis of 4-n-alkoxy benzoic acid (3c) General procedure: 4-n-alkoxy benzoic acids (3c) were prepared by dissolving comp.3b in ethanol (40 ml) and10% aq.KOH(2ml)was added. The resultant mixturewas heated at reflux for 6 to 7 hours thencooled to room temperature, poured into ice cold water (80 ml) and then acidified with dil.HCl. The crude product obtained by filtration was recrystallized by usingMeOH/DCM [51].
With potassium hydroxide In ethanol Reflux;
With potassium hydroxide In ethanol; water Reflux; 2.2.3 Synthesis of 4-n-alkoxy benzoic acid (1c) General procedure: 4-n-alkoxy benzoic acids (3c) were prepared by dissolving comp.3b in ethanol (40 ml)and 10% aq. KOH (2 ml) was added. The resultant mixture was heated at reflux for 6 to 7 hours then cooled to room temperature, poured into ice cold water (80 ml) and thenacidified with dil.HCl. The crude product obtained by filtration was recrystallized byusing MeOH/DCM
With ethanol; potassium hydroxide for 2h; Reflux;
With ethanol; potassium hydroxide Reflux;

  • 5
  • [ 106-94-5 ]
  • [ 99-76-3 ]
  • [ 5438-19-7 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; butanone Erwaermen des Reaktionsprodukts mit methanol. Kalilauge;
With hydrogenchloride; potassium hydroxide; sodium hydroxide In ethanol; water; dimethyl sulfoxide 24.i (i) (i) Synthesis of 4-n-propyloxybenzoic acid Methyl 4-hydroxybenzoate (15.4 g: 101.2 mmol) was dissolved in 150 ml of dimethylsulfoxide (DMSO), and an aqueous solution of potassium hydroxide (KOH/H2O: 7 g/15 ml) was added to the mixture. The resultant mixture was stirred until dissolving homogeneously. Next, 12.5 g (101.6 mmol) of n-propyl bromide was added thereto, and the reaction was carried out at a room temperature for 24 hours. The reaction mixture was poured into 1 L of an iced water and the resultant precipitate was collected by filtration. The obtained precipitate was dissolved in 300 ml of ethanol, and an aqueous solution of sodium hydroxide (NaOH/H2O: 5 g/100 ml) was added thereto. Thus obtained mixture was refluxed by heating for 1 hour, and water (the amount of the water: about 300 ml) was added thereto with removing ethanol (EtOH). After cooling to a room temperature, the transparent solution was acidified by adding a concentrated hydrochloric acid. The resultant white precipitate was filtered and recrystallized from toluene to give 17.5 g (97.2 mmol) of 4-n-propyloxybenzoic acid.
2.20 g With potassium carbonate In acetone for 48h; Reflux; General Procedure for the Synthesis of 4-O-Substituted Benzoic Acids 5a-d General procedure: MeOH (40 mL) concentrated sulfuric acid was added (0.1 equiv.). The reaction mixture was heated at reflux for 24 h, and then cooled to rt. The solvent was removed under reduced pressure. A saturated aqueous solution of NaHCO3 (40 mL) was added and the aqueous layer was extracted with diethyl eter (3 × 15 mL). The organic extracts were dried over anhydrous Na2SO4, filtered, and the solvent was removed under reduced pressure. Crude ester was dissolved in acetone (30 mL) and potassium carbonate (1.5 equiv.) and 1-bromoethane (3 equiv.) were added. The reaction mixture was heated at reflux for 48 h, and then cooled to rt. The solvent was removed under reduced pressure and water was added. The aqueous layer was extracted with CH2Cl2 (3 × 15 mL). The organic extracts were dried over anhydrous Na2SO4, filtered, and the solvent was removed under reduced pressure. The obtained crude product was then dissolved in 96 % EtOH (35 mL) and aqueous solution of NaOH (15 mL, 40 %) was added. The reaction mixture was heated at reflux overnight. Mixture was cooled, and pH was adjusted to 1 by addition of concentrated HCl to the reaction mixture. The precipitate was filtered, washed with water and dried to yield crude 5a-d. The compounds 5a-d were purified by crystallization from boiling 96 % EtOH.
  • 6
  • [ 106-94-5 ]
  • [ 99-96-7 ]
  • [ 5438-19-7 ]
YieldReaction ConditionsOperation in experiment
70% With potassium hydroxide In ethanol; water for 15h; Reflux; 9 Add 4-hydroxybenzoic acid (1.38g, 10mmol), potassium hydroxide (1.12g, 20mmol), ethanol (20mL), water (10mL) to a 100mL single-mouth flask, add bromopropane (2.44g, 20mmol) dropwise, and reflux After 15 hours of reaction, after the raw materials are completely reacted, add water (30mL), adjust the pH to 2.0 with concentrated hydrochloric acid, precipitate solids, filter, wash with water, wash with n-hexane, and dry to obtain solid 4-propoxybenzoic acid (1.26g). Yield 70%.
With potassium hydroxide
With potassium hydroxide; Aliquat 336 1.) 80 deg C, 24 h; 2.) ethanol, 80 deg C, 24 h; Multistep reaction;
With potassium hydroxide; ethanol
With potassium hydroxide In ethanol
With potassium hydroxide In ethanol Heating;
With potassium hydroxide In ethanol
With potassium hydroxide In methanol Heating;
Stage #1: 4-hydroxy-benzoic acid With potassium hydroxide In methanol Stage #2: propyl bromide In methanol Heating; Further stages.;
With potassium hydroxide In methanol Reflux;
With potassium hydroxide In ethanol
With potassium hydroxide In ethanol
Stage #1: propyl bromide; 4-hydroxy-benzoic acid With potassium hydroxide at 70℃; Reflux; Stage #2: Acidic aq. solution; Cooling with ice;
Stage #1: 4-hydroxy-benzoic acid With potassium hydroxide Stage #2: propyl bromide In ethanol Reflux;
With potassium hydroxide In ethanol
With potassium hydroxide In methanol
With potassium hydroxide Reflux;
In methanol Reflux;
With potassium hydroxide
With potassium hydroxide In ethanol
With potassium hydroxide
With potassium hydroxide In methanol
With potassium hydroxide In methanol Reflux;
With potassium hydroxide In methanol; ethanol Reflux;
With potassium hydroxide In methanol Reflux; 2.3.1. synthesis of 4-n-alkoxy benzoic acid (A) General procedure: 4-n-alkoxy benzoic acid were synthesized by refluxing the mixture of 4-hydroxy benzoic acid(1 equiv.) with corresponding n-alkyl bromides (1 equiv.) in the presence of KOH (1.5 equiv.)and MeOH/ EtOH as a solvent [52].
With potassium hydroxide In methanol; ethanol Reflux; 2.3.3. Synthesis of -n-alkoxy benzoic acid derivatives (C) General procedure: 4-n-alkoxy benzoic acid were synthesized by refluxing the mixture of 4-hydroxy benzoic acid(1 equiv.) with corresponding n-alkyl bromides (1 equiv.) in the presence of KOH (1.5 equiv.)and MeOH/ EtOH as a solvent [38].
With potassium hydroxide In methanol Reflux;
Stage #1: 4-hydroxy-benzoic acid With potassium hydroxide In methanol Stage #2: propyl bromide In methanol at 64 - 66℃; Stage #3: In water for 2h; Reflux; 4.2.1. Synthesis of 4-n-alkyloxybenzoic acid (7b-m) General procedure: To a solution of 4-hydroxy benzoic acid (3.5 g, 0.03 mmol, 1 eq)in methanol (25 mL) was added KOH (3.5 g, 0.06 mmol, 2.5 eq) andstirred for 8-10 min. To this solition, alkyl bromide (0.03 mmol,1.2 eq) was added and resulting mixture was refluxed at 64-66 C for 6-7 h. During this time, solid was separated out in reactionmixture. To this reaction mixture, 20% aq solution of KOH(5 mL) was added and refluxed for another 2 h to give clear solution.The reaction mixture was allowed to cool down to room temperatureand was acidified by 10% HCl solution (25 mL) followedby addition of ice-cold water to give solid. The solid separatedout was filtered, dried and recrystallized from absolute ethanolto give pure compound 7b-m.
In methanol Reflux; 2.3.1. Synthesis of 4-n-alkoxy benzoic acid (A) General procedure: 4-hydroxy benzoic acid alkylated by alkylating agent (R-Br), KOH, MeOH (C1 to C8)and Ethanol (C10 to C16), increasing reflux time period with increasing chain to yield corresponding 4-n-alkoxy benzoic acids (A), which was confirmed by IR and 1H NMR study [36].
With potassium iodide; potassium hydroxide In ethanol for 12h; Reflux; 2.1.1. General method for the synthesis of 4-alkoxybenzoic acid (A1-A18) General procedure: To a stirred solution of 1-alkylbromide (90 mmol) and 4-hydroxybenzoic acid(36.20 mmol) in ethanol (200 mL) was added KOH (72.40 mmol) followed by potassiumiodide (KI) (1.5 mmol). Reflux the reaction mixture for 12 h. After completion of thereaction monitored by TLC, cool the reaction mixture at room temperature and treatedwith aqueous HCl solution up to pH 1. The white precipitation was obtained, whichwas filtered off and dried under vacuum to give 4-alkyloxybenzoic acid (A1-A18). Allthe derivatives were used without further purification for the next step. All the productswere confirmed by ESI-MS analysis.
With potassium hydroxide In ethanol 2.2.4 4-n-Alkoxybenzoic acids [d] General procedure: 4-n-alkoxybenzoic acids [D] were synthesized from 4-hydroxybenzoic acid by employing a Williamson’s ether synthesis protocol [79].
With potassium hydroxide In ethanol; water Reflux;

Reference: [1]Current Patent Assignee: ZHEJIANG UNIVERSITY OF TECHNOLOGY - CN111995567, 2020, A Location in patent: Paragraph 0128-0129; 0132
[2]McElvain; Carney [Journal of the American Chemical Society, 1946, vol. 68, p. 2592,2599]
[3]Bayle, J.-P.; Bui, E.; Perez, F.; Courtieu, J. [Bulletin de la Societe Chimique de France, 1989, # 4, p. 532 - 536]
[4]Tinh; Pourrere; Destrade [Molecular Crystals and Liquid Crystals (1969-1991), 1980, vol. 62, # 1-2, p. 125 - 139]
[5]Dave, Jayrang S.; Menon, Meera R.; Patel, Pratik R. [Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 2002, vol. 378, p. 1 - 11]
[6]Prajapati; Pandya [Molecular Crystals and Liquid Crystals, 2003, vol. 393, p. 31 - 39] Prajapati; Sharma; Chudgar [Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 2001, vol. 364, p. 815 - 823]
[7]Dave, Jayrang S.; Menon, Meera R.; Patel, Pratik R. [Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 2001, vol. 364, p. 575 - 587]
[8]Prajapati, Ashish K. [Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 2000, vol. 348, p. 65 - 72]
[9]Thaker; Patel, Pranay; Vansadia; Patel [Molecular Crystals and Liquid Crystals, 2007, vol. 466, # 1, p. 13 - 22]
[10]Thaker; Patel, Pranay [Molecular Crystals and Liquid Crystals, 2008, vol. 482, # 1, p. 3 - 20]
[11]Location in patent: experimental part Ganatra; Bhoya [Molecular Crystals and Liquid Crystals, 2008, vol. 487, p. 110 - 116]
[12]Location in patent: experimental part Dixit, Sandhya; Vora [Molecular Crystals and Liquid Crystals, 2009, vol. 501, p. 43 - 52]
[13]Location in patent: scheme or table Prajapati; Bonde [Molecular Crystals and Liquid Crystals, 2009, vol. 501, p. 72 - 85]
[14]Location in patent: experimental part Thaker; Patel, Pranay [Molecular Crystals and Liquid Crystals, 2009, vol. 509, # 1, p. 173 - 185]
[15]Location in patent: scheme or table Thaker; Patel; Kanojiya [Molecular Crystals and Liquid Crystals, 2009, vol. 509, # 1, p. 145 - 164]
[16]Location in patent: scheme or table Dave, Jayrang S.; Upasani; Patel, Purvang D. [Molecular Crystals and Liquid Crystals, 2010, vol. 533, p. 73 - 81] Location in patent: scheme or table Thaker; Patel; Dhimmar; Solnki; Chothani; Patel; Patel; Makavana [Molecular Crystals and Liquid Crystals, 2012, vol. 562, p. 98 - 113]
[17]Location in patent: scheme or table Chauhan; Doshi [Molecular Crystals and Liquid Crystals, 2012, vol. 552, p. 16 - 23] Location in patent: scheme or table Doshi; Makwana [Molecular Crystals and Liquid Crystals, 2011, vol. 548, p. 220 - 227]
[18]Location in patent: scheme or table Thaker; Solanki; Patel; Vansadia; Dhimmar [Molecular Crystals and Liquid Crystals, 2012, vol. 552, p. 134 - 146]
[19]Location in patent: scheme or table Chauhan; Pandya; Doshi [Molecular Crystals and Liquid Crystals, 2011, vol. 548, p. 228 - 234]
[20]Location in patent: scheme or table Dave, Jayrang S.; Bhatt, Himanshu S. [Molecular Crystals and Liquid Crystals, 2012, vol. 562, p. 1 - 9] Location in patent: scheme or table Dave, Jayrang S.; Patel, Purvang D.; Bhatt, Himanshu [Molecular Crystals and Liquid Crystals, 2012, vol. 562, p. 76 - 84]
[21]Thaker; Chothani; Patel; Dhimmar; Solanki; Patel, Neeraj; Patel; Makawana [Molecular Crystals and Liquid Crystals, 2013, vol. 575, # 1, p. 64 - 76] Dixit, Sandhya; Vora [Molecular Crystals and Liquid Crystals, 2014, vol. 592, # 1, p. 133 - 140] Dixit, Sandhya; Vora [Molecular Crystals and Liquid Crystals, 2015, vol. 623, # 1, p. 56 - 63] Dixit; Intwala [Molecular Crystals and Liquid Crystals, 2016, vol. 631, # 1, p. 1 - 8] Patel; Prajapati [Molecular Crystals and Liquid Crystals, 2017, vol. 643, # 1, p. 106 - 115] Dixit, Sandhya [Molecular Crystals and Liquid Crystals, 2018, vol. 664, # 1, p. 77 - 84] Crawford, Catriona A.; Gorecka, Ewa; Imrie, Corrie T.; Pociecha, Damian; Storey, John M. D.; Walker, Rebecca [Journal of Molecular Liquids, 2020, vol. 303] Yao, Yong fang; Patel; Prajapati, Ashish Kumar; Sangani, Chetan B.; Duan, Yong-Tao [Molecular Crystals and Liquid Crystals, 2021, vol. 712, # 1, p. 31 - 42]
[22]Bhatt, Himanshu S.; Patel, Purvang D.; Dave, Jayrang S. [Molecular Crystals and Liquid Crystals, 2013, vol. 575, # 1, p. 104 - 111]
[23]Chauhan; Doshi, Ankita A.; Doshi [Molecular Crystals and Liquid Crystals, 2013, vol. 570, # 1, p. 84 - 91] Prajapati; Doshi [Molecular Crystals and Liquid Crystals, 2015, vol. 608, # 1, p. 62 - 71] Prajapati; Doshi [Molecular Crystals and Liquid Crystals, 2015, vol. 616, # 1, p. 28 - 36] Prajapati; Doshi [Molecular Crystals and Liquid Crystals, 2015, vol. 616, # 1, p. 37 - 45] Makwana; Doshi [Molecular Crystals and Liquid Crystals, 2015, vol. 616, # 1, p. 55 - 63] Makwana; Doshi [Molecular Crystals and Liquid Crystals, 2015, vol. 616, # 1, p. 93 - 101] Doshi; Chauhan [Molecular Crystals and Liquid Crystals, 2015, vol. 606, # 1, p. 66 - 74] Makwana; Prajapati; Doshi [Molecular Crystals and Liquid Crystals, 2015, vol. 623, # 1, p. 119 - 128] Makwana; Prajapati; Chahar; Doshi [Molecular Crystals and Liquid Crystals, 2015, vol. 623, # 1, p. 148 - 156] Patel; Prajapati; Doshi [Molecular Crystals and Liquid Crystals, 2016, vol. 624, # 1, p. 51 - 58] Patel; Doshi, Ankita A.; Prajapati; Doshi [Molecular Crystals and Liquid Crystals, 2016, vol. 624, # 1, p. 69 - 76] Maheta; Bhoya [Molecular Crystals and Liquid Crystals, 2016, vol. 625, # 1, p. 72 - 80] Jain; Patel [Molecular Crystals and Liquid Crystals, 2016, vol. 630, # 1, p. 121 - 129] Jain; Patel [Molecular Crystals and Liquid Crystals, 2016, vol. 633, # 1, p. 63 - 71] Solanki, Ravindra; Patel [Molecular Crystals and Liquid Crystals, 2016, vol. 634, # 1, p. 24 - 32]
[24]Kotadiya; Bhoya [Molecular Crystals and Liquid Crystals, 2015, vol. 608, # 1, p. 116 - 124] Kotadiya; Khunt; Bhoya [Molecular Crystals and Liquid Crystals, 2015, vol. 607, # 1, p. 135 - 143] Kotadiya; Bhoya [Molecular Crystals and Liquid Crystals, 2015, vol. 616, # 1, p. 19 - 27] Vadodaria; Ladva; Doshi; Travadi [Molecular Crystals and Liquid Crystals, 2016, vol. 624, # 1, p. 59 - 68] Vadodaria; Ladva; Doshi; Travadi [Molecular Crystals and Liquid Crystals, 2016, vol. 624, # 1, p. 103 - 111] Khunt; Kotadiya; Bhoya [Molecular Crystals and Liquid Crystals, 2016, vol. 625, # 1, p. 20 - 29] Travadi; Vadodaria; Ladva; Doshi [Molecular Crystals and Liquid Crystals, 2016, vol. 625, # 1, p. 63 - 71] Travadi; Vadodaria; Ladva; Doshi [Molecular Crystals and Liquid Crystals, 2016, vol. 626, # 1, p. 21 - 30] Khunt; Kotadiya; Bhoya [Molecular Crystals and Liquid Crystals, 2016, vol. 626, # 1, p. 31 - 44] Kotadiya; Khunt; Bhoya [Molecular Crystals and Liquid Crystals, 2016, vol. 626, # 1, p. 45 - 57] Travadi; Vadodaria; Ladva; Doshi [Molecular Crystals and Liquid Crystals, 2016, vol. 626, # 1, p. 58 - 67] Khunt; Kotadiya; Bhoya [Molecular Crystals and Liquid Crystals, 2016, vol. 626, # 1, p. 68 - 80] Travadi; Vadodaria; Ladva; Doshi [Molecular Crystals and Liquid Crystals, 2016, vol. 626, # 1, p. 90 - 99] Travadi; Vadodaria; Ladva; Doshi [Molecular Crystals and Liquid Crystals, 2016, vol. 630, # 1, p. 69 - 78] Maheta; Bhoya [Molecular Crystals and Liquid Crystals, 2016, vol. 633, # 1, p. 29 - 36] Sharma, Vinay S.; Patel [Molecular Crystals and Liquid Crystals, 2017, vol. 643, # 1, p. 62 - 75] Namera, Dipti L.; Ranchchh, Avani R.; Bhoya [Molecular Crystals and Liquid Crystals, 2017, vol. 643, # 1, p. 233 - 240] Sharma, Vinay. S.; Vekariya, Rajesh. H.; Sharma, Anuj. S.; Patel [Molecular Crystals and Liquid Crystals, 2017, vol. 652, # 1, p. 84 - 98] Sharma, Vinay S.; Vekariya, Rajesh H.; Sharma, Anuj S.; Patel [Molecular Crystals and Liquid Crystals, 2017, vol. 652, # 1, p. 143 - 157] Sharma, Vinay S.; Sharma, Anuj S.; Vekariya, Rajesh H.; Patel [Molecular Crystals and Liquid Crystals, 2017, vol. 658, # 1, p. 32 - 44] Kher, Seema N.; Prajapati; Chandra, Raviprakash S.; Makwana [Molecular Crystals and Liquid Crystals, 2018, vol. 665, # 1, p. 1 - 9] Kher, Seema N.; Prajapati; Makwana; Chandra, Raviprakash S. [Molecular Crystals and Liquid Crystals, 2019, vol. 682, # 1, p. 44 - 53]
[25]Solanki; Sharma, Vinay. S.; Patel [Molecular Crystals and Liquid Crystals, 2017, vol. 643, # 1, p. 216 - 232]
[26]Sharma, Vinay S.; Sharma, Anuj S.; Patel [Molecular Crystals and Liquid Crystals, 2017, vol. 652, # 1, p. 158 - 171]
[27]Sharma, Vinay S.; Sharma, Anuj S.; Patel [Molecular Crystals and Liquid Crystals, 2017, vol. 658, # 1, p. 45 - 58]
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[30]Dwivedi, Durgesh J.; Thakor, Akshay; Desai, Vipul; Sharma, Vinay S.; Patel [Molecular Crystals and Liquid Crystals, 2021, vol. 723, # 1, p. 16 - 32]
[31]Bhalodiya, Pradip C.; Patel, Hemant N.; Parmar, Tejasvi H.; Sangani, Chetan B.; Rajani, Dhanji P. [Molecular Crystals and Liquid Crystals, 2021, vol. 724, # 1, p. 1 - 25]
[32]Duan, Yongtao; Koshti, Rohit R.; Kumar Ameta, Rakesh; Patel, H. N.; Sangani, Chetan B.; Tarpada, Umesh P.; Vyas, Akshay; Yao, Yongfang [Journal of Molecular Liquids, 2021, vol. 336]
[33]Jiang, Xiaoying; Guo, Jianan; Zhang, Changjun; Gu, Jinping; Zhou, Tao; Bai, Renren; Xie, Yuanyuan [Journal of Enzyme Inhibition and Medicinal Chemistry, 2021, vol. 36, # 1, p. 2045 - 2054]
  • 7
  • [ 5438-19-7 ]
  • 3,4-dihydro-1-(4-piperidyl)-2(1H)-quinoline hydrochloride [ No CAS ]
  • 1-[1-(4-Propoxybenzoyl)-4-piperidinyl]-3,4-dihydrocarbostyril [ No CAS ]
YieldReaction ConditionsOperation in experiment
With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine In dichloromethane for 1h; Ambient temperature;
  • 8
  • [ 5438-19-7 ]
  • [ 123-08-0 ]
  • [ 56800-28-3 ]
YieldReaction ConditionsOperation in experiment
87.1% Stage #1: (-)-4-(1-propyloxy)benzoic acid; 4-hydroxy-benzaldehyde With 4-dimethylaminopyridine In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; 4.3.5 General procedure for the synthesis of aldehyde scaffolds 7a-7n and 8a-8n General procedure: 3-Hydroxybenzaldehyde (for 7a-7n) or 4-hydroxybenzaldehyde (for 8a-8n) (1.0g, 8.19mmol), DMAP (0.05g, 0.4mmol) and the corresponding 4-alkoxy benzoic acid (8.19mmol) were dissolved in DMF and stirred at room temperature for 15min. Then DCC (2.0g, 9.83mmol) was added drop wise to the reaction mixture. After completion of reaction, the reaction mixture was diluted with ethyl acetate and filtered through celite. The filtrate was washed with water and brine solution. The organic portion was dried over sodium sulfate and concentrated under reduced pressure. The crude was then purified by column chromatography (silica gel 100-200 mesh) using ethyl acetate in hexanes to obtain the product.
In chloroform
With dicyclohexyl-carbodiimide In dichloromethane at 20℃;
With 4-dimethylaminopyridine; dicyclohexyl-carbodiimide In dichloromethane at 20℃;
With 4-dimethylaminopyridine; dicyclohexyl-carbodiimide In dichloromethane for 12h;
With 4-dimethylaminopyridine; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 25h;
With 4-dimethylaminopyridine; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 25h; Inert atmosphere;
With 4-dimethylaminopyridine; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h; 2.3. General procedure for the synthesis of of 4-formylphenyl-4-(alkyloxy)benzoates, 8- (2-18) General procedure: To a solution of 4-n-alkoxybenzoic acid 7 (0.01 mol, 1.0 eq)) inDCM (30 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) (0.015 mol) and few crystals of 4-dimethylaminopyridine (DMAP), as catalyst followed by 4-hydroxybenzaldehyde (0.01 mol). The reaction mixture was thenstirred at room temperature for 24 h. The mixture was poured oncrushed ice and extracted with dichloromethane (2 30 mL).The organic layer was dried over anhy. Na2SO4, filtered and evaporatedto give solid residue. The solid was recrystallized from ethanol to give 4-formylphenyl-4-(alkyloxy)benzoate, 8-(2-18).
With 4-dimethylaminopyridine; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h; 2.5. General procedure for the synthesis of of 4-formylphenyl-4-(alkyloxy)benzoates, 16- (2-18) General procedure: 4-Formylphenyl-4-(alkyloxy)benzoates, 16-(2-18) were prepared by following general procedure reported with minor modification [24] . Equimolar quantities of 4-n-alkoxybenzoic acid 14 and 4- hydroxybenzaldehyde 15 (0.01 mol) were dissolved in 30 ml dry dichloromethane. 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) (0.015 mol) and few crystals of 4-dimethylaminopyridine (DMAP) were added as catalyst. The reaction mixture was then stirred for 24 h at room temperature. The reaction mixture was poured on ice water and extracted twice by dichloromethane. Evaporation of the combined organic layer resulted in 4- formylphenyl-4-(alkyloxy)benzoate, 16-(2-18) . The obtained solid product was recrystallized from ethanol
With 4-dimethylaminopyridine; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h; 2.3. General procedure for the synthesis of 4-formylphenyl-4-(alkyloxy)benzoates, 7(2-18) General procedure: 4-Formylphenyl-4-(alkyloxy)benzoates, 7(2-18) were prepared by following general procedure reported. Equimolar quantities of 4-n-alkoxybenzoic acid 5 and 4-hydroxybenzaldehyde 6 (0.01 mol) were dissolved in 30 ml dry dichloromethane. 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) (0.015 mol) and few crystals of 4-dimethylaminopyridine (DMAP), as catalyst, were added. The reaction mixture was then stirred for 24 h at room temperature. The mixture was poured on crushed ice and extracted twice by dichloromethane. Evaporation of the combined organic layer resulted in 4-formylphenyl-4-(alkyloxy)benzoate, 7(2-18). The obtained solid product was recrystallized from ethanol.

  • 9
  • [ 5438-19-7 ]
  • [ 95-01-2 ]
  • [ 177424-30-5 ]
YieldReaction ConditionsOperation in experiment
With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide In diethyl ether for 24h; Ambient temperature;
With dicyclohexyl-carbodiimide In dichloromethane at 20℃;
Stage #1: 4-propoxybenzoic acid; 2,4-Dihydroxybenzaldehyde With dmap In dichloromethane for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Inert atmosphere; Cooling with ice;
  • 10
  • [ 5438-19-7 ]
  • [ 848478-61-5 ]
  • 4-(3-hydroxyoctanoyl)phenyl 4-propoxybenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 23h;
  • 11
  • [ 5438-19-7 ]
  • [ 848478-63-7 ]
  • 4-(3-chlorooctanoyl)phenyl 4-propoxybenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;
  • 12
  • [ 27914-60-9 ]
  • [ 5438-19-7 ]
  • [ 99-96-7 ]
YieldReaction ConditionsOperation in experiment
1: 82% 2: 3% With potassium hydroxide In methanol at 20℃; for 10h;
  • 13
  • [ 914784-11-5 ]
  • [ 5438-19-7 ]
  • 4-(5-pentylisoxazol-3-yl)phenyl 4-propoxybenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With dmap; dicyclohexyl-carbodiimide In dichloromethane
  • 14
  • C62H92O16 [ No CAS ]
  • [ 5438-19-7 ]
  • C72H102O18 [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With bis-2-propyl carbonate; 4-(dimethylamino)pyridinium tosylate In dichloromethane
  • 15
  • C92H152O26 [ No CAS ]
  • [ 5438-19-7 ]
  • C102H162O28 [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With bis-2-propyl carbonate; 4-(dimethylamino)pyridinium tosylate In dichloromethane
  • 16
  • C128H224O38 [ No CAS ]
  • [ 5438-19-7 ]
  • C138H234O40 [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With bis-2-propyl carbonate; 4-(dimethylamino)pyridinium tosylate In dichloromethane
Historical Records