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Product Details of [ 5438-19-7 ]

CAS No. :5438-19-7 MDL No. :MFCD00013989
Formula : C10H12O3 Boiling Point : -
Linear Structure Formula :C3H7OC6H4COOH InChI Key :GDFUWFOCYZZGQU-UHFFFAOYSA-N
M.W : 180.20 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 ]

* 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 [ 5438-19-7 ]

[ 5438-19-7 ] Synthesis Path-Downstream   1~101

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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%.

Reference: [1]Rohmann; Scheurle [Archiv der Pharmazie, 1936, vol. 274, p. 110,123]
[2]Cohen; Dudley [Journal of the Chemical Society, 1910, vol. 97, p. 1747]
[3]Dong, C. C.; Sun, Z. M.; Li, G. Z. [Molecular Crystals and Liquid Crystals (1969-1991), 1990, vol. 185, p. 35 - 45]
[4]Zuniga, C.; Bartulin, J.; Mueller, H. J.; Schumacher, E.; Taylor, T. R. [Molecular Crystals and Liquid Crystals (1969-1991), 1991, vol. 206, p. 131 - 137] Malthete, Jacques; Canceill, Josette; Gabard, Jacqueline; Jacques, Jean [Tetrahedron, 1981, vol. 37, # 16, p. 2815 - 2821] Tinh; Pourrere; Destrade [Molecular Crystals and Liquid Crystals (1969-1991), 1980, vol. 62, # 1-2, p. 125 - 139]
[5]Munakata; Tanaka; Toyoshima [Chemical and Pharmaceutical Bulletin, 1980, vol. 28, # 7, p. 2045 - 2051]
[6]Deschenaux, Robert; Marendaz, Jean-Luc; Santiago, Julio [Helvetica Chimica Acta, 1993, vol. 76, # 2, p. 865 - 876]
[7]Kaharu, Takeshi; Matsubara, Hiroshi; Takahashi, Shigetoshi [Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1992, vol. 220, p. 191 - 199] 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] Prajapati; Pandya [Molecular Crystals and Liquid Crystals, 2003, vol. 393, p. 31 - 39] 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] Prajapati; Sharma; Chudgar [Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 2001, vol. 364, p. 815 - 823]
[8]Sakaguchi; Nishino; Ogawa; Iwanaga; Yasuda; Kato; Ito [Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 1, p. 202 - 211]
[9]Kalyvas; McIntyre [Molecular Crystals and Liquid Crystals (1969-1991), 1982, vol. 80, # 1-4, p. 105 - 118]
[10]Arora, S. L.; Ziemnicka, B.; Doane, J. W. [Molecular Crystals and Liquid Crystals (1969-1991), 1985, vol. 127, p. 341 - 353]
[11]Sakagami, Sakumitshu [Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 3, p. 1153 - 1154]
[12]Mundhe [Journal of the Indian Chemical Society, 1999, vol. 76, # 5, p. 246 - 249]
[13]Blake; Bruce; Danks; Fallis; Guillon; Ross; Richtzenhain; Schroeder [Journal of Materials Chemistry, 2001, vol. 11, # 4, p. 1011 - 1018]
[14]Moorhoff, Cornelis M.; Braybrook, Carl [Monatshefte fur Chemie, 2004, vol. 135, # 4, p. 397 - 405]
[15]Kovganko; Kovganko [Russian Journal of Organic Chemistry, 2006, vol. 42, # 6, p. 907 - 911]
[16]Prajapati, Ashish K. [Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 2000, vol. 348, p. 65 - 72] Tandel; Vora [Molecular Crystals and Liquid Crystals, 2008, vol. 482, # 1, p. 103 - 116]
[17]Patel; Doshi [Journal of the Indian Chemical Society, 2007, vol. 84, # 11, p. 1122 - 1125] Tandel; Mammen, Denni [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2008, vol. 47, # 6, p. 932 - 937]
[18]Location in patent: experimental part Patel; Doshi [Journal of the Indian Chemical Society, 2008, vol. 85, # 7, p. 746 - 749]
[19]Location in patent: experimental part Ganatra; Bhoya [Molecular Crystals and Liquid Crystals, 2008, vol. 487, p. 110 - 116] Location in patent: experimental part Dixit, Sandhya; Vora [Molecular Crystals and Liquid Crystals, 2009, vol. 501, p. 43 - 52]
[20]Location in patent: scheme or table Prajapati; Bonde [Molecular Crystals and Liquid Crystals, 2009, vol. 501, p. 72 - 85]
[21]Location in patent: body text Kovganko; Kovganko; Polovkov [Russian Journal of Organic Chemistry, 2010, vol. 46, # 12, p. 1812 - 1816]
[22]Location in patent: scheme or table Thaker; Patel; Kanojiya [Molecular Crystals and Liquid Crystals, 2009, vol. 509, # 1, p. 145 - 164]
[23]Location in patent: scheme or table Tikhomirova; Maizlish; Shaposhnikov [Russian Journal of General Chemistry, 2011, vol. 81, # 4, p. 768 - 772] 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 Chauhan; Doshi [Molecular Crystals and Liquid Crystals, 2012, vol. 552, p. 16 - 23]
[24]Location in patent: experimental part Sabatini, Stefano; Gosetto, Francesca; Manfroni, Giuseppe; Tabarrini, Oriana; Kaatz, Glenn W.; Patel, Diixa; Cecchetti, Violetta [Journal of Medicinal Chemistry, 2011, vol. 54, # 16, p. 5722 - 5736]
[25]Location in patent: scheme or table Thaker; Solanki; Patel; Vansadia; Dhimmar [Molecular Crystals and Liquid Crystals, 2012, vol. 552, p. 134 - 146]
[26]Location in patent: experimental part Bhoya; Vyas; Doshi [Molecular Crystals and Liquid Crystals, 2012, vol. 552, p. 104 - 110]
[27]Location in patent: scheme or table Chauhan; Pandya; Doshi [Molecular Crystals and Liquid Crystals, 2011, vol. 548, p. 228 - 234] Location in patent: scheme or table Doshi; Makwana [Molecular Crystals and Liquid Crystals, 2011, vol. 548, p. 220 - 227] 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]
[28]Suthar; Doshi [Molecular Crystals and Liquid Crystals, 2012, vol. 569, # 1, p. 64 - 71] Chauhan; Patel; Doshi [Molecular Crystals and Liquid Crystals, 2013, vol. 574, # 1, p. 67 - 74] Suthar; Doshi, Ankita A.; Doshi [Molecular Crystals and Liquid Crystals, 2013, vol. 574, # 1, p. 75 - 83] Chauhan; Vyas; Doshi [Molecular Crystals and Liquid Crystals, 2013, vol. 575, # 1, p. 96 - 103] Chaudhari; Chauhan; Doshi [Molecular Crystals and Liquid Crystals, 2013, vol. 575, # 1, p. 88 - 95] Chauhan; Doshi [Molecular Crystals and Liquid Crystals, 2013, vol. 570, # 1, p. 12 - 19] Chauhan; Doshi [Molecular Crystals and Liquid Crystals, 2013, vol. 570, # 1, p. 92 - 100] Chaudhari; Doshi; Doshi [Molecular Crystals and Liquid Crystals, 2013, vol. 582, # 1, p. 63 - 71] Suthar; Doshi; Doshi [Molecular Crystals and Liquid Crystals, 2013, vol. 582, # 1, p. 79 - 87] Kotadiya; Khunt; Bhoya [Molecular Crystals and Liquid Crystals, 2014, vol. 593, # 1, p. 165 - 176] Khunt; Kotadiya; Bhoya [Molecular Crystals and Liquid Crystals, 2015, vol. 607, # 1, p. 32 - 40] Maheta; Bhola; Namera; Bhoya [Molecular Crystals and Liquid Crystals, 2015, vol. 607, # 1, p. 104 - 113] Kotadiya; Bhoya [Molecular Crystals and Liquid Crystals, 2015, vol. 608, # 1, p. 116 - 124] Bhola; Nakum, Kiran; Karia, Kaushal; Bhoya [Molecular Crystals and Liquid Crystals, 2015, vol. 608, # 1, p. 125 - 134] Patel, Brijesh H.; Vyas; Doshi [Molecular Crystals and Liquid Crystals, 2015, vol. 607, # 1, p. 114 - 122] Kotadiya; Khunt; Bhoya [Molecular Crystals and Liquid Crystals, 2015, vol. 607, # 1, p. 135 - 143] Patel, Brijesh H.; Patel; Doshi [Molecular Crystals and Liquid Crystals, 2015, vol. 609, # 1, p. 10 - 18] Kotadiya; Bhoya [Molecular Crystals and Liquid Crystals, 2015, vol. 616, # 1, p. 19 - 27] Marathe, Rajesh B.; Doshi [Molecular Crystals and Liquid Crystals, 2015, vol. 616, # 1, p. 74 - 82] Khunt; Kotadiya; Bhoya [Molecular Crystals and Liquid Crystals, 2014, vol. 605, # 1, p. 32 - 41] Kotadiya; Khunt; Bhoya [Molecular Crystals and Liquid Crystals, 2014, vol. 605, # 1, p. 52 - 60] Patel, Brijesh H.; Doshi [Molecular Crystals and Liquid Crystals, 2014, vol. 605, # 1, p. 61 - 69] Kotadiya; Khunt; Bhoya [Molecular Crystals and Liquid Crystals, 2015, vol. 606, # 1, p. 47 - 55] Patel, H. Brijesh; Doshi [Molecular Crystals and Liquid Crystals, 2015, vol. 606, # 1, p. 56 - 65] Chauhan; Doshi; Sheth [Molecular Crystals and Liquid Crystals, 2015, vol. 623, # 1, p. 157 - 165] Marathe, Rajesh B.; Doshi [Molecular Crystals and Liquid Crystals, 2016, vol. 624, # 1, p. 122 - 131] Rakhasia; Bhoya [Molecular Crystals and Liquid Crystals, 2016, vol. 625, # 1, p. 55 - 62] Sharma; Solanki; Patel; Patel [Molecular Crystals and Liquid Crystals, 2016, vol. 625, # 1, p. 137 - 145] Jain; Sharma, Vinay S.; Chauhan; Patel [Molecular Crystals and Liquid Crystals, 2016, vol. 630, # 1, p. 102 - 111]
[29]Patel; Vyas; Doshi [Molecular Crystals and Liquid Crystals, 2012, vol. 569, # 1, p. 15 - 23] Syrbu; Potemkina; Novikov; Kuvshinova; Koifman; Aleksandriiskii; Burmistrov [Russian Journal of Organic Chemistry, 2013, vol. 49, # 2, p. 208 - 211][Zh. Org. Khim., 2013, vol. 49, # 2, p. 219 - 222,4] Chauhan; Doshi, Ankita A.; Doshi [Molecular Crystals and Liquid Crystals, 2013, vol. 570, # 1, p. 84 - 91] Chaudhari; Doshi [Molecular Crystals and Liquid Crystals, 2013, vol. 570, # 1, p. 109 - 116] Suthar; Doshi [Molecular Crystals and Liquid Crystals, 2013, vol. 571, # 1, p. 1 - 8] 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] Chauhan; Doshi [Molecular Crystals and Liquid Crystals, 2015, vol. 623, # 1, p. 166 - 175] 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] Vadodaria; Ladva; Doshi; Travadi [Molecular Crystals and Liquid Crystals, 2016, vol. 624, # 1, p. 59 - 68] Patel; Doshi, Ankita A.; Prajapati; Doshi [Molecular Crystals and Liquid Crystals, 2016, vol. 624, # 1, p. 69 - 76] Vadodaria; Ladva; Doshi; Travadi [Molecular Crystals and Liquid Crystals, 2016, vol. 624, # 1, p. 103 - 111] Chauhan; Patel; Pandya; Doshi [Molecular Crystals and Liquid Crystals, 2016, vol. 625, # 1, p. 47 - 54] Travadi; Vadodaria; Ladva; Doshi [Molecular Crystals and Liquid Crystals, 2016, vol. 625, # 1, p. 63 - 71] Marathe; Doshi [Molecular Crystals and Liquid Crystals, 2016, vol. 625, # 1, p. 81 - 92] Travadi; Vadodaria; Ladva; Doshi [Molecular Crystals and Liquid Crystals, 2016, vol. 626, # 1, p. 21 - 30] Travadi; Vadodaria; Ladva; Doshi [Molecular Crystals and Liquid Crystals, 2016, vol. 626, # 1, p. 58 - 67] Rakhasia; Bhola; Bhoya [Molecular Crystals and Liquid Crystals, 2016, vol. 626, # 1, p. 81 - 89] 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] Jain; Patel [Molecular Crystals and Liquid Crystals, 2016, vol. 630, # 1, p. 121 - 129] Patel, Priya K.; Shah [Molecular Crystals and Liquid Crystals, 2016, vol. 630, # 1, p. 130 - 138] Dixit; Intwala [Molecular Crystals and Liquid Crystals, 2016, vol. 631, # 1, p. 1 - 8] Solanki, Ravindra; Sharma, Vinay; Patel, Roshan [Molecular Crystals and Liquid Crystals, 2016, vol. 631, # 1, p. 107 - 115] Patel, Priya K.; Shah [Molecular Crystals and Liquid Crystals, 2017, vol. 643, # 1, p. 168 - 177]
[30]Bhatt, Himanshu S.; Patel, Purvang D.; Dave, Jayrang S. [Molecular Crystals and Liquid Crystals, 2013, vol. 575, # 1, p. 104 - 111]
[31]Funke, Mario; Thimm, Dominik; Schiedel, Anke C.; Müller, Christa E. [Journal of Medicinal Chemistry, 2013, vol. 56, # 12, p. 5182 - 5197]
[32]Tengler, Jan; Kapustikova, Iva; Stropnicky, Ondrej; Mokry, Petr; Oravec, Michal; Csoellei, Jozef; Jampilek, Josef [Central European Journal of Chemistry, 2013, vol. 11, # 11, p. 1757 - 1767]
[33]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, Sandhya [Molecular Crystals and Liquid Crystals, 2018, vol. 664, # 1, p. 77 - 84]
[34]Adamski, Ariel; Bogucki, Andrzej; ͆wietlik, Roman; Wróbel, Rafał J.; Klapiszewski, Łukasz; Jesionowski, Teofil; Tylkowski, Bartosz; Kubicki, Maciej; Patroniak, Violetta [Supramolecular Chemistry, 2015, vol. 27, # 9, p. 571 - 583]
[35]Kadam, Vinay S.; Shaikh, Saminaparwin G.; Patel, Arun L. [Journal of Molecular Structure, 2016, vol. 1114, p. 181 - 188]
[36]Tikhomirova; Gruzdeva; Shaposhnikov [Russian Journal of General Chemistry, 2015, vol. 85, # 12, p. 2778 - 2785][Zh. Obshch. Khim., 2015, vol. 85, # 12, p. 2049 - 2056,8]
[37]Jadeja; Patel [Molecular Crystals and Liquid Crystals, 2016, vol. 638, # 1, p. 17 - 26]
[38]Zhu, Jie; Li, Sunsun; Liu, Xiaoyu; Yao, Huifeng; Wang, Fenghao; Zhang, Shaoqing; Sun, Mingliang; Hou, Jianhui [Journal of Materials Chemistry A, 2017, vol. 5, # 29, p. 15175 - 15182]
[39]Current Patent Assignee: ELI LILLY & CO - WO2006/101808, 2006, A1 Location in patent: Page/Page column 37
[40]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]
[41]Nguyen, T. Vu; Minrovic, Bradley M.; Melander, Roberta J.; Melander, Christian [ChemMedChem, 2019, vol. 14, # 9, p. 927 - 937]
[42]Thakur, Shavi; Patel, Hemant N. [Molecular Crystals and Liquid Crystals, 2020, vol. 712, # 1, p. 76 - 89]
[43]Current Patent Assignee: SOUTHWEST JIAOTONG UNIVERSITY - CN113105391, 2021, A Location in patent: Paragraph 0286-0291
[44]Darwish, Salma; Erdmann, Frank; Ghazy, Ehab; Heimburg, Tino; Jung, Manfred; Lancelot, Julien; Pierce, Raymond; Robaa, Dina; Romier, Christophe; Schmidt, Matthias; Schmidtkunz, Karin; Shaik, Tajith B.; Simoben, Conrad V.; Sippl, Wolfgang; Truhn, Anne; Zeyen, Patrik [European Journal of Medicinal Chemistry, 2021, vol. 225]
  • 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]
[28]Thakur, Shavi; Patel, Hemant N. [Molecular Crystals and Liquid Crystals, 2020, vol. 712, # 1, p. 76 - 89]
[29]Shah, Priyanka; Soni, Rina; Soman, Shubhangi S [Journal of Molecular Liquids, 2021, vol. 335]
[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
  • 17
  • [ 67-56-1 ]
  • [ 5438-19-7 ]
  • [ 115478-59-6 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid Heating;
With sulfuric acid for 4h; Reflux; 4.1.1. General procedure for the synthesis of methyl esters (2a-o) General procedure: Each substituted benzoic acid (1) (0.04 mol) was heated at reflux for 4 hours in 50.0 mL (1.23 mol) of anhydrous methanol and 1.0 mL (2.0 mmol) of sulfuric acid. The solvent was concentrated and the product obtained washed with cold water. In some cases, as for non-substituted compounds, the ester showed an oily aspect and, to promote its precipitation, the compound was cooled by immersion in dry ice-ethanol bath.
With thionyl chloride at 0℃; for 1h; Reflux;
  • 18
  • [ 5438-19-7 ]
  • [ 33905-61-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: SOCl2 2: pyridine
Multi-step reaction with 3 steps 1: SOCl2 / 2 h / Heating 2: NEt3 / CH2Cl2 / 2 h / Heating 3: H2 / 10percent Pd-C / CH2Cl2; ethanol / 15001.2 Torr
Multi-step reaction with 2 steps 1: thionyl chloride 2: pyridine / 10 h / 30 °C
  • 19
  • [ 99-76-3 ]
  • [ 5438-19-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) NaH / 1.) THF, 0 deg C, 2.) reflux, 4 h
Multi-step reaction with 2 steps 1: sodium methylate 2: alkali
Multi-step reaction with 2 steps 1: potassium hydroxide / methanol / Reflux 2: potassium hydroxide / ethanol; water / 2 h / Reflux
Multi-step reaction with 2 steps 1: potassium hydroxide / methanol / Reflux 2: potassium hydroxide / ethanol / Reflux
Multi-step reaction with 2 steps 1: methanol / Reflux 2: potassium hydroxide / ethanol; water / Reflux
Multi-step reaction with 2 steps 1: potassium hydroxide / methanol / Reflux 2: potassium hydroxide; ethanol / 2 h / Reflux
Multi-step reaction with 2 steps 1: potassium hydroxide / methanol / Reflux 2: potassium hydroxide; ethanol / Reflux

  • 20
  • [ 120-47-8 ]
  • [ 5438-19-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium ethylate; ethanol 2: ethanolic KOH-solution
Multi-step reaction with 2 steps 1: sodium ethylate; ethanol 2: aq. NaOH solution
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide 2: sodium hydroxide; ethanol
  • 21
  • [ 5438-19-7 ]
  • [ 64328-60-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: methanol. HCl 2: methanol; N2H4+H2O
Multi-step reaction with 2 steps 1: sulfuric acid / 4 h / Reflux 2: hydrazine hydrate / water / 0.17 h / 75 °C
Stage #1: 4-propoxybenzoic acid With sulfuric acid In methanol for 4h; Reflux; Stage #2: With hydrazine hydrate In methanol; water at 20℃; for 0.5h; 4 4.1.1 General procedure for the preparation of benzhydrazides (2u-z) General procedure: Each substituted benzoic acid (0.01 mol) was refluxed during 4 h in 20.0 mL (0.50 mol) of anhydrous methanol and 0.5 mL (1.0 mmol) of sulfuric acid. The reaction mixture was cooled down to room temperature and the hydrazine hydrate 80% (v/v) (10.0 mL, 0.11 mol) was added. The system was maintained into vigorously stirring for more 30 min. After this period, the mixture was maintained at cold temperature to give 2.
Stage #1: 4-propoxybenzoic acid With sulfuric acid In methanol at 20℃; for 4h; Reflux; Stage #2: With hydrazine hydrate In methanol at 75℃; for 0.5h; 4.1.1. General procedure for the synthesis of hydrazides General procedure: each carboxylic acid (a) (0.02 mol) was refluxed for 4 h in 20.0 mL (0.49 mol) of anhydrous methanol and 0.5 mL (0.01 mol) of sulfuric acid. The reaction mixture was cooled down to room temperature and the hydrazine hydrate 80% (v/v) (10.0 mL, 0.13 mol) was added. The system was maintained by vigorously stirring for more 30 min in reflux. After this period, the mixture was maintained at low temperature to give (b), and was purified from ethyl acetate. The hydrazide intermediate of compounds 1 and 2 were commercially obtained (Sigma-Aldrich, purity of 97%) [47].

  • 22
  • [ 443682-63-1 ]
  • [ 5438-19-7 ]
  • (R)-4-(3-ethyl-1-methylpentyloxycarbonyl)phenyl-4-n-propyloxybenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h; 32 Example 32; (Formula (1): n=3, A =-O-, X=H, Y=H, B=-COO- (E19)); Preparation of (R)-4-(3-ethyl-1-methylpentyloxycarbonyl)phenyl-4-n-propyloxybenzoate 1.44 Grams (8.0 mmol) of 4-n-propyloxybenzoic acid, 1.65 g (8.0 mmol) of N,N-dicyclohexylcarbodiimide (DCC) and 30 ml of dichloromethane were placed in a reactor, 2.0 g (8.0 mmol) of (R)-3-ethyl-1-methylpentyl-4-hydroxybenzoate was added, then, 0.20 g (1.6 mmol) of 4-dimethylaminopyridine was added, and the mixture was stirred at room temperature for 12 hours. [00145] After completion of the reaction, a precipitated solid was separated by filtration and washed with diethyl ether. To a filtrate was added 60 ml of diethyl ether, and the mixture was washed with 2N hydrochloric acid, with a 1N sodium hydroxide aqueous solution and then with water. An organic layer was dried over anhydrous sodium sulfate and filtered, and the solvent was distilled off, to give 3.2 g of crude (R)-4-(3-ethyl-1-methylpentyloxycarbonyl)phenyl-4-n-propyloxybenzoate (yield 97%). [00146] The thus-obtained crude product was purified with a liquid chromatograph, to give 2.5 g of (R)-4-(3-ethyl-1-methylpentyloxycarbonyl)phenyl-4-n-propyloxybenzoate as an end product (yield 76%).
  • 23
  • [ 4143-61-7 ]
  • [ 436848-04-3 ]
  • [ 5438-19-7 ]
  • [ 469858-99-9 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran 24.iii (iii) (iii) Synthesis of 4'-(tert-butoxycarbonyloxy)phenyl-4-n-propyloxybenzoate To 1.64 g (10 mmol) of 4-propyloxybenzoic acid and 2.1 g (10 mmol) of 4-(tert-butoxycarbonyloxy)phenol obtained by the steps (i) and (ii), respectively, was added 2.62 g (10 mmol) of triphenylphosphine (PPh3), and the mixture was homogeneously dissolved in 50 ml of dried tetrahydrofuran (THF). Next, azodicarboxylic acid diethyl ester (1.74 g:10 mmol) was added dropwise to the mixture with cooling with ice, and the reaction was conducted at a room temperature for 24 hours. After completion of the reaction, the solvent was evaporated. The resultant residue was purified by silica gel column chromatography (eluent: toluene), and recrystallized from methanol to give 1.9 g (5.1 mmol) of 4'-(tert-butoxycarbonyloxy)phenyl-4-n-propyloxybenzoate. 1H-NMR(CDCl3) ppm: 1.08 (t, 3H, CH3), 1.55 (s, 9H, tert-Bu), 1.80-1.94 (m, 2H, CH2), 4.02 (t, 2H, OCH2), 6.98 (d, 2H, C6H4), 7.25 (d, 4H, C6H4), 8.15 (d, 2H, C6H4).
  • 24
  • [ 5438-19-7 ]
  • [ 369358-82-7 ]
YieldReaction ConditionsOperation in experiment
294 N'-((2RS,3R)-3-amino-5-(ethylsulfanyl)-2-hydroxypentanoyl)-4-propoxybenzohydrazide EXAMPLE 294 N'-((2RS,3R)-3-amino-5-(ethylsulfanyl)-2-hydroxypentanoyl)-4-propoxybenzohydrazide The desired product was prepared by substituting 4-propoxybenzoic acid for 3-(ethylsulfanyl)benzoic acid in Example 239B. MS(ESI) m/e 370 (M+H)+; 1H NMR (500 MHz, CD3OD) δ 7.86 (m, 2H), 7.01 (m, 2H), 4.48 (d, 0.35), 4.44 (d, 0.65), 4.01 (dt, 2H), 3.77 (m, 1H), 2.71 (t, 2H), 2.60 (dd, 211), 2.16 (dd, 1H), 1.99 (dt, 1H), 1.82 (ddd, 2H), 1.28 (t, 1.95H), 1.25 (t, 1.05H) 1.05 (t, 3H).
  • 25
  • [ 5438-19-7 ]
  • [ 369358-84-9 ]
YieldReaction ConditionsOperation in experiment
296 N'-((2RS,3R)-3-amino-5-(ethylsulfanyl)-2-hydroxypentanoyl)-4-isopropoxybenzohydrazide EXAMPLE 296 N'-((2RS,3R)-3-amino-5-(ethylsulfanyl)-2-hydroxypentanoyl)-4-isopropoxybenzohydrazide The desired product was prepared by substituting 4-(2-methylethoxy)benzoic acid for 3-(ethylsulfanyl)benzoic acid in Example 239B. MS(ESI) m/e 370 (M+H)+; 1H NMR (500 MHz, CD3OD) δ 7.84 (m, 2H), 6.99 (m, 2H), 4.71 (ddd, 1H), 4.48 (d, 0.35), 4.44 (d, 0.65), 3.78 (m, 1H), 2.71 (t, 2H), 2.61 (dd, 2H), 2.16 (dd, 1H), 2.00 (dt, o 1H), 1.34 (d, 6H), 1.28 (t, 1.95H), 1.25 (t, 1.05H).
  • 26
  • [ 5438-19-7 ]
  • [ 369360-05-4 ]
YieldReaction ConditionsOperation in experiment
N'-((2RS,3R)-3-amino-2-hydroxy-5-(isopropylsulfanyl)pentanoyl)-4-propoxybenzohydrazide N'-((2RS,3R)-3-amino-2-hydroxy-5-(isopropylsulfanyl)pentanoyl)-4-propoxybenzohydrazide The desired compound was prepared by substituting p-propoxybenzoic acid for o-toluic acid in Example 369. MS(ESI) m/e 384 (M+H)+; 1H NMR (500 MHz, CD3OD) δ 7.85 (m, 2H), 7.00 (m, 2H), 7.31 (m, 1H), 4.48 (d, 0.3H), 4.44 (d, 0.7H), 4.01 (m,2H), 3.78 (m, 1H), 3.00 (m, 1H), 2.71 (t, 2H), 2.15 (m, 1H), 1.97 (m, 1H), 1.82 (m, 2H), 1.29-1.24 (m, 6H), 1.05 (t, 3H).
  • 27
  • [ 910802-66-3 ]
  • [ 5438-19-7 ]
  • methyl ({6-ethyl-4-[4-(4-propoxybenzoyl)piperazin-1-yl]thieno[2,3-d]pyrimidin-2-yl}thio)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide for 20h; 71 EXAMPLE 71; Methyl ({6-ethyl-4-[4-(4-propoxybenzoyl)piperazin-1-yl]thieno[2,3-d]pyrimidin-2-yl}thio)acetateTo a mixture of the hydrochloride salt of Example 34 (0.10 g) in DMF (3.0 mL) in a 2 dram screw cap vial was added diisopropylethylamine (0.15 mL), 4-propoxy benzoic acid (0.048 g), and HATU (0.1 g). The mixture was placed in a Lab-Line MAX Q2000 orbital shaker for 20 hours at which time the mixture was partitioned between brine and ethyl acetate. The layers were separated and the organic layer washed four times with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was chromatographed on silica gel using 1 :1 ethyl acetate: hexanes as eluent to give 0.0733 g (55%) of the title compound: MS (ESI+) for C25 H30 N4 04 S2 /77/Z515.17 (M+H)+. 1H NMR (CDCI3) δ 1.05 (t, 3 H), 1.33 (t, 3 H), 1.83 (m, 2 H), 2.85 (q, 2 H), 3.72 (s, 3 H), 3.77 (m, 4 H), 3.88 (m, 4 H), 3.90
  • 28
  • [ 67-56-1 ]
  • terbium(III) nitrate hexahydrate [ No CAS ]
  • [ 5438-19-7 ]
  • [Tb(4-ethoxybenzoate)2(NO3)](CH3OH)2]n [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With sodium hydroxide In methanol acid-compd. and 1 equiv. of NaOH were stirred in MeOH at room temp. for 30 min, 1/3 equiv. of metal-nitrate was added in MeOH, 1 d, stirring forfurther 12 h; ppt. was filtered off and washed with MeOH, elem. anal.;
  • 29
  • [ 67-56-1 ]
  • gadolinium(III) nitrate hexahydrate [ No CAS ]
  • [ 5438-19-7 ]
  • [Gd(4-ethoxybenzoate)2(NO3)](CH3OH)2]n [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With sodium hydroxide In methanol acid-compd. and 1 equiv. of NaOH were stirred in MeOH at room temp. for 30 min, 1/3 equiv. of metal-nitrate was added in MeOH, 1 d, stirring forfurther 12 h; ppt. was filtered off and washed with MeOH, elem. anal.;
  • 30
  • [ 67-56-1 ]
  • europium(III) nitrate hexahydrate [ No CAS ]
  • [ 5438-19-7 ]
  • [Eu(4-ethoxybenzoate)2(NO3)](CH3OH)2]n [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With sodium hydroxide In methanol acid-compd. and 1 equiv. of NaOH were stirred in MeOH at room temp. for 30 min, 1/3 equiv. of metal-nitrate was added in MeOH, 1 d, stirring forfurther 12 h; ppt. was filtered off and washed with MeOH, elem. anal.;
  • 31
  • [ 99-96-7 ]
  • [ 5438-19-7 ]
YieldReaction ConditionsOperation in experiment
80% With potassium hydroxide In ethanol Heating;
With potassium hydroxide In methanol
With potassium hydroxide In methanol Reflux;
In methanol

Reference: [1]Tandel; Mammen, Denni [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2008, vol. 47, # 6, p. 932 - 937]
[2]Patel; Chauhan; Doshi [Molecular Crystals and Liquid Crystals, 2012, vol. 569, # 1, p. 57 - 63] Suthar; Doshi [Molecular Crystals and Liquid Crystals, 2012, vol. 569, # 1, p. 64 - 71] Chaudhari; Doshi; Doshi [Molecular Crystals and Liquid Crystals, 2013, vol. 582, # 1, p. 63 - 71] Suthar; Doshi; Doshi [Molecular Crystals and Liquid Crystals, 2013, vol. 582, # 1, p. 79 - 87] Jadeja; Sharma, Vinay S.; Jain; Patel [Molecular Crystals and Liquid Crystals, 2016, vol. 630, # 1, p. 144 - 153] Jadeja; Patel [Molecular Crystals and Liquid Crystals, 2016, vol. 638, # 1, p. 17 - 26] Sharma, Vinay S.; Jadeja; Patel [Molecular Crystals and Liquid Crystals, 2017, vol. 643, # 1, p. 28 - 39] Jain; Jadeja; Patel [Molecular Crystals and Liquid Crystals, 2017, vol. 652, # 1, p. 1 - 9]
[3]Chauhan; Vyas; Doshi [Molecular Crystals and Liquid Crystals, 2013, vol. 575, # 1, p. 96 - 103] Chaudhari; Doshi [Molecular Crystals and Liquid Crystals, 2013, vol. 570, # 1, p. 109 - 116] Al-Malki, Mustafa K.S.; Hameed, Ayad S.; Al-Dujaili, Ammar H. [Molecular Crystals and Liquid Crystals, 2014, vol. 593, # 1, p. 34 - 42] Kotadiya; Khunt; Bhoya [Molecular Crystals and Liquid Crystals, 2014, vol. 593, # 1, p. 165 - 176] Bhola; Nakum, Kiran; Karia, Kaushal; Bhoya [Molecular Crystals and Liquid Crystals, 2015, vol. 608, # 1, p. 125 - 134] Patel, Brijesh H.; Vyas; Doshi [Molecular Crystals and Liquid Crystals, 2015, vol. 607, # 1, p. 114 - 122] Patel, Brijesh H.; Patel; Doshi [Molecular Crystals and Liquid Crystals, 2015, vol. 609, # 1, p. 10 - 18] Marathe, Rajesh B.; Doshi [Molecular Crystals and Liquid Crystals, 2015, vol. 616, # 1, p. 74 - 82] Kotadiya; Khunt; Bhoya [Molecular Crystals and Liquid Crystals, 2014, vol. 605, # 1, p. 52 - 60] Patel, Brijesh H.; Doshi [Molecular Crystals and Liquid Crystals, 2014, vol. 605, # 1, p. 61 - 69] Kotadiya; Khunt; Bhoya [Molecular Crystals and Liquid Crystals, 2015, vol. 606, # 1, p. 47 - 55] Marathe, Rajesh B.; Doshi [Molecular Crystals and Liquid Crystals, 2016, vol. 624, # 1, p. 122 - 131] Sharma; Solanki; Patel; Patel [Molecular Crystals and Liquid Crystals, 2016, vol. 625, # 1, p. 137 - 145] Rakhasia; Bhola; Bhoya [Molecular Crystals and Liquid Crystals, 2016, vol. 626, # 1, p. 81 - 89] Jain; Sharma, Vinay S.; Chauhan; Patel [Molecular Crystals and Liquid Crystals, 2016, vol. 630, # 1, p. 102 - 111]
[4]Patel, Priya K.; Shah [Molecular Crystals and Liquid Crystals, 2016, vol. 630, # 1, p. 130 - 138] Patel, Priya K.; Shah [Molecular Crystals and Liquid Crystals, 2017, vol. 643, # 1, p. 168 - 177]
  • 32
  • [ 5438-19-7 ]
  • [ 32223-64-6 ]
YieldReaction ConditionsOperation in experiment
With diphenyl phosphoryl azide; triethylamine In toluene at 20 - 105℃; for 1.16667h; Inert atmosphere;
  • 33
  • [ 4254-15-3 ]
  • [ 5438-19-7 ]
  • [ 1243060-59-4 ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃;
  • 34
  • [ 5438-19-7 ]
  • [ 128625-52-5 ]
  • [ 618-39-3 ]
  • [ 876179-80-5 ]
  • [ 1263815-73-1 ]
  • 35
  • [ 5438-19-7 ]
  • [ 124-42-5 ]
  • C12H16N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 25℃; for 2h;
  • 36
  • [ 5438-19-7 ]
  • [ 57297-29-7 ]
  • C14H18N2O2 [ No CAS ]
  • 37
  • [ 5438-19-7 ]
  • [ 618-39-3 ]
  • [ 1263815-73-1 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 25℃; for 2h;
  • 38
  • [ 5438-19-7 ]
  • [ 932042-48-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: thionyl chloride 2: magnesium ethylate / tetrahydrofuran; tetrachloromethane; ethanol / 0 - 20 °C 3: potassium hydroxide / ethanol / 24 h / 20 °C
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / Reflux 2.1: magnesium chloride; triethylamine / tetrahydrofuran / 6 h / 25 °C 2.2: Reflux
  • 39
  • [ 5438-19-7 ]
  • [ 104-42-7 ]
  • 12A + (3BA)2 [ No CAS ]
  • 40
  • [ 5438-19-7 ]
  • [ 551-93-9 ]
  • [ 1319210-02-0 ]
YieldReaction ConditionsOperation in experiment
72% With triethylamine In tetrahydrofuran at 70℃; for 3h;
  • 41
  • 1-benzyl piperazine dihydrobromide [ No CAS ]
  • [ 5438-19-7 ]
  • [ 617675-58-8 ]
YieldReaction ConditionsOperation in experiment
11% Stage #1: 4-propoxybenzoic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: 1-benzyl piperazine dihydrobromide With triethylamine In N,N-dimethyl-formamide at 20℃; General coupling procedure for compounds 1a-i: General procedure: To a solution of appropriate carboxylic acid (2 mmol) in 5 mL dry DMF was added EDCI (0.46 g; 2.4 mmol), and the reaction mixture was stirred at room temperature for 15 min. 1-Benzyl piperazine dihydrobromide (0.68 g; 2 mmol) and TEA (1.0 mL, 7.2 mmol) were added to above solution and the reaction mixture was stirred at room temperature overnight. The solvent was removed and the residue was taken up with ethyl acetate (30 mL) and water (20 mL). The organic layer was washed with brine (20 mL), dried over anhydrous sodium sulfate. The drying agent was filtered off and the filtrate was concentrated to dryness. The crude product was purified by flash chromatography (silica gel/ethyl acetate/hexanes) to give pure products 1a-i.
  • 42
  • [ 5438-19-7 ]
  • [ 1017029-32-1 ]
  • [ 1397262-86-0 ]
YieldReaction ConditionsOperation in experiment
71% With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 20h; Inert atmosphere; General procedure for amide formation General procedure: To a suspension of EDC*HCl (0.92 g, 4.8 mmol, 1.2 equiv.) and NMM (1.76 mL, 16 mmol, 4 equiv.) in dry N,N-dimethylformamide (20 mL) at RT were added successively HOBt (0.65 g, 4.8 mmol, 1.2 equiv.), carboxylic acid (4.4 mmol, 1.1 equiv.) and N-(2-aminoethyl)benzofuran-2-carboxamide 23 (0.81 g, 4 mmol, 1 equiv.). The reaction mixture was stirred at RT for 20 h and then diluted with water (100 mL) and extracted with CHCl3:MeOH (9:1 v/v, 3 x 50 mL). The combined organic fractions were washed with aqueous sodium hydroxide (1 M, 100 mL), dried (Na2SO4) and concentrated under reduced pressure to give a crude residue which was triturated with cold ethyl acetate (ca. 10 mL).
  • 44
  • [ 99-96-7 ]
  • [ 5438-19-7 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide In methanol Reflux;
With potassium hydroxide In methanol
Multi-step reaction with 3 steps 1: sulfuric acid / 1 h / Reflux 2: potassium hydroxide / methanol / Reflux 3: potassium hydroxide / ethanol; water monomer / 2 h / Reflux
Multi-step reaction with 3 steps 1: sulfuric acid / Reflux 2: potassium hydroxide / methanol / Reflux 3: potassium hydroxide / ethanol / Reflux
Multi-step reaction with 3 steps 1: sulfuric acid / 3 h / Reflux 2: methanol / Reflux 3: potassium hydroxide / ethanol; water monomer / Reflux
Multi-step reaction with 3 steps 1: sulfuric acid / 1 h / Reflux 2: potassium hydroxide / methanol / Reflux 3: potassium hydroxide; ethanol / 2 h / Reflux
Multi-step reaction with 3 steps 1: sulfuric acid / Reflux 2: potassium hydroxide / methanol / Reflux 3: potassium hydroxide; ethanol / Reflux
Multi-step reaction with 2 steps 1: sulfuric acid / 24 h / Reflux 2: potassium carbonate / acetone / 48 h / Reflux
Stage #1: 4-hydroxy-benzoic acid With potassium hydroxide In ethanol for 10h; Stage #2: With potassium carbonate In acetone for 24h;

  • 45
  • [ 102-71-6 ]
  • [ 5438-19-7 ]
  • [ 1440507-27-6 ]
YieldReaction ConditionsOperation in experiment
85% Stage #1: triethanolamine; 4-propoxybenzoic acid In chloroform for 0.166667h; Stage #2: With dmap; dicyclohexyl-carbodiimide In chloroform for 12h;
  • 46
  • [ 5438-19-7 ]
  • potassium trans-hex-1-enyltrifluoroborate [ No CAS ]
  • [ 1440548-48-0 ]
YieldReaction ConditionsOperation in experiment
81% With dmap; oxygen; copper(I) bromide In acetonitrile at 60℃; for 24h; Molecular sieve; stereospecific reaction;
  • 47
  • [ 5438-19-7 ]
  • potassium trifluoro(prop-1-en-1-yl)borate [ No CAS ]
  • [ 1440548-71-9 ]
YieldReaction ConditionsOperation in experiment
71% With dmap; oxygen; copper(I) bromide In acetonitrile at 60℃; for 24h; Molecular sieve; stereospecific reaction;
  • 48
  • [ 5438-19-7 ]
  • [ 77103-47-0 ]
  • [ 1462352-06-2 ]
YieldReaction ConditionsOperation in experiment
73% With dmap; dicyclohexyl-carbodiimide In dichloromethane for 25h;
  • 49
  • [ 123-91-1 ]
  • [ 5438-19-7 ]
  • [ 1597710-63-8 ]
YieldReaction ConditionsOperation in experiment
91% With iron(III)-acetylacetonate; di-tert-butyl peroxide at 120℃; for 24h; Schlenk technique;
  • 50
  • [ 5438-19-7 ]
  • C6H13N2O3Pol [ No CAS ]
  • C16H23N2O5Pol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With ethyl cyanoglyoxylate-2-oxime; diisopropyl-carbodiimide In dichloromethane at 20℃; for 24h; 4.2.3. General procedure for the coupling of benzoic acid derivatives General procedure: A solution of the respective carboxylic acid (1.2 mmol), Oxyma(171 mg, 1.2 mmol) and DIC (151 mg, 1.2 mmol) in CH2Cl2 (10 mL) was added to the resin and shaken for 24 h. The resin was washed with CH2Cl2 (3 x 5 mL), MeOH (3 x 5 mL), CH2Cl2 (3 x 5 mL).
  • 51
  • [ 5438-19-7 ]
  • [ 79-19-6 ]
  • [ 299936-27-9 ]
YieldReaction ConditionsOperation in experiment
60% Stage #1: 4-propoxybenzoic acid; thiosemicarbazide With trichlorophosphate for 5h; Reflux; Stage #2: With water for 7h; Cooling; Reflux; Synthesis of 5-(4-n-alkoxyphenyl)-2-amino-1,3,4-thiadiazole [III]n General procedure: A mixture ofappropriate 4-n-alkoxybenzoic acid (10 mmol) and (0.91 g, 10 mmol) of thiosemicarbazidewith 5 mL of phosphorus oxychloride was refluxed gently for 5 hr. After cooling 50 mL of water was added, the mixture was then refluxed for 7 hr and filtered, neutralizedwith potassium hydroxide. The precipitate was washed with water and recrystallized fromethanol-water to give titled compound [III]n.
  • 52
  • [ 5438-19-7 ]
  • [ 500195-02-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sulfuric acid / methanol / 4 h / 20 °C / Reflux 1.2: 0.5 h / 75 °C 2.1: acetic acid; sulfuric acid / methanol; water / 1 h / Reflux
  • 53
  • [ 5438-19-7 ]
  • [ 115914-43-7 ]
  • nonane-1,9-diyl bis(4,1-phenylene) bis(4-propoxybenzoate) [ No CAS ]
YieldReaction ConditionsOperation in experiment
80.4% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane
  • 54
  • [ 5438-19-7 ]
  • [ 5424-02-2 ]
  • C25H21ClO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h;
  • 55
  • [ 97727-87-2 ]
  • [ 5438-19-7 ]
  • C23H20O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h;
  • 56
  • [ 5438-19-7 ]
  • [ 88521-99-7 ]
  • C26H24O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h; Synthesis General procedure: 4-Hydroxy benzoic acid was alkylated using suitable alkylating agents (R-X) by the modifiedmethod of Dave and Vora [22]. Condensation of 4-methyl benzaldehyde and 4-hydroxyacetophenon for the synthesis of α-4-hydroxy benzoyl β-4-methyl phenyl ethylene waseffected by the usual conventional method [23]. A mixture of 4-n-alkoxy benzoic acids, α-4-hydroxy benzoyl-β-4-methyl phenyl ethylene, 1,3-dicyclohexylcarbodiimide (DCC), 4-dimethylaminopyridine (DMAP) in dichloromethane was used for the synthesis of α-4-(4-n-Alkoxy benzoyloxy) benzoyl β-4-methyl phenyl ethylenes [24]. The synthetic route tothe series is shown in Scheme 1. The final chalconyl derivatives were decomposed, filtered,washed, dried and crystallized until constant transition temperatures obtained.The chemicals 4-hydroxy benzoic acid, 4-hydroxy acetophenon, 4-methyl benzaldehyde,alkyl bromide (R-Br), methanol, KOH, 1,3-dicyclohexylcarbodiimide, 4-dimethylaminopyridine, dichloromethane, ethanol etc. were used as received except solvents,which were dried, purified and distilled prior to use
  • 57
  • [ 97727-84-9 ]
  • [ 5438-19-7 ]
  • C25H21BrO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h; General procedure: n-alkoxy benzoic acids were prepared from 4-hydroxy benzoic acid and suitable alkylating agents by modified method of Dave and Vora [28]. α-4-hydroxy benzoyl β-4-bromo phenyl ethylene was prepared by usual established method [29]. 4-n-Alkoxy benzoic acids and α-4-hydroxy benzoyl-β-4-bromo phenyl ethylene were condensed in 1,3-dicyclohexylcarbodiimide (DCC), 4-dimethylaminopyridine (DMAP), and CH2Cl2 [30]. Synthetic route to usual series is mentioned below as Scheme 1. Final products were individually decomposed, filtered, washed, dried, and purified until the constant transition temperatures were obtained.
  • 58
  • [ 5438-19-7 ]
  • α-(4-hydroxybenzoyl)-β-(2,5-dimethoxyphenyl)ethylene [ No CAS ]
  • C27H26O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h;
  • 59
  • [ 118712-54-2 ]
  • [ 5438-19-7 ]
  • oxiran-2-ylmethyl 4-propoxybenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% Stage #1: 4-propoxybenzoic acid With potassium hydroxide In methanol; isopropyl alcohol at 20℃; for 1h; Stage #2: glycidyl p-toluenesulfonate In N,N-dimethyl-formamide at 70℃; for 7h; Oxiran-2-ylmethyl 4-propoxybenzoate (2) A mixture of 4-propoxybenzoic acid (5 g, 0.028 mol) in methanol (75 mL) and KOH (2.2 g, 0.042 mol) in propan-2-ol (50 mL) was stirred for 1 h at room temperature, and after that, propan-2-ol (175 mL) was added for the final ratio methanol:propan-2-ol 1:3. The resulting white precipitate was collected by filtration and dried under low pressure. A mixture of appropriate potassium salt (5 g, 0.023 mol) with (oxiran-2-yl)methyl 4-methyl benzensulfonate (1, 2.6 g, 0.011 mol) in DMF (27 mL) was heated for 7 h at 70 °C. The reaction was monitored by TLC. The solvent was evaporated, and the residue was dissolved in ethyl acetate and washed with water; the organic layer was dried over MgSO4, and ethyl acetate was evaporated. Yield: 83%; Rf: 0.77 (ethyl acetate/petroleum ether 1:1); 1H-NMR (200 MHz, DMSO-d6) δ: 7.92 (d, 3J = 8.8 Hz, 2H, Ar-COO), 7.04 (d, 3J = 8.8 Hz, 2H, Ar-O), 4.60 (dd, 2J = 12.4, 3J = 2.7 Hz, 1H, COOCH2), 4.04 (dd, 2J = 12.4 Hz, 3J = 6.4 Hz, 1H, COOCH2), 4.00 (t, 3J = 6.5 Hz, 1H, CH2CH2), 3.36-3.28 (m, 1H, CH-oxiran), 2.83 (dd, 2J = 5.2 Hz, 3J = 4.3 Hz, 1H, CH2-oxiran), 2.72 (dd, 2J = 5.0 Hz, 3J = 2.7 Hz, 1H, CH2-oxiran), 1.83-1.65 (m, 2H, CH2CH3), 0.97 (t, 3J = 7.3 Hz, 3H, CH3); 13C-NMR (50 MHz, DMSO-d6) δ: 165.01, 162.68, 131.22, 121.28, 114.35, 69.24, 64.87, 48.97, 43.73, 21.76, 10.10.
  • 60
  • [ 5438-19-7 ]
  • 2-hydroxynaphthyl azo-4-butyloxybenzene [ No CAS ]
  • C30H30N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h;
  • 61
  • [ 5438-19-7 ]
  • α-4-hydroxylbenzoyl β-4'-heptyloxyphenylethylene [ No CAS ]
  • C32H36O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h;
  • 62
  • [ 13160-68-4 ]
  • [ 5438-19-7 ]
  • C22H20N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h;
  • 63
  • [ 5438-19-7 ]
  • α-3-nitro-4-hydroxybenzoyl-β-4'-dodecyloxyphenylethylene [ No CAS ]
  • C37H45NO7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h;
  • 64
  • [ 5438-19-7 ]
  • [ 3021-36-1 ]
  • C26H28N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Synthesis General procedure: 4-Hydroxy benzoic acid was alkylated using the appropriate alkylating agent(R-X) to convertit into 4-n-alkoxy benzoic acids(A) by a modified method of Dave and Vora [25]. Alkylationof paracetamol using alkylating agent n-C4H9Br was carried out to form 4-n-butyloxyacetanilide, which on hydrolysis was converted to 4-n-butyloxy aniline by a usual establishmethod. Azodye (B) 4-hydroxy phenyl azo 4-butyloxy benzene (m.p. 126°C, yield 73%) wasprepared by well-known azotization method [26], Final azoester products were synthesizedby condensation of (A) and (B) [27]. Thus, the azo-ester homologue derivatives were filtered,washed with sodium bicarbonate solution followed by distilled water, dried and purified untilconstant transition temperatures obtained, using an optical polarizing microscope equippedwith a heating stage. 4-Hydroxy benzoic acid, alkyl halides, paracetamol, phenol, NaNO2,dicyclohexylcarbodimide (DCC), dimethyl amino pyridine (DMAP), K2CO3, DCM, MeOH,acetone required for synthesis were used as received except solvents which were dried anddistilled prior to use. The synthetic route to the series is shown in Scheme 1.
  • 65
  • [ 5438-19-7 ]
  • [ 7397-22-0 ]
  • C25H21FO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide In dichloromethane
  • 66
  • [ 5438-19-7 ]
  • 4-hydroxy napthyl azo 4’-n-butyloxy benzene [ No CAS ]
  • C30H30N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h;
  • 67
  • [ 5438-19-7 ]
  • 1-(4-hydroxy-3-nitrophenyl)-3-(4-(pentyloxy)phenyl)prop-2-en-1-one [ No CAS ]
  • C30H31NO7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 48h; Synthesis of ester derivatives General procedure: The compound has been prepared by esterification of the appropriate 4-n-alkoxycinnamic acid (A) (2.02 mmol) and chalcone (C) (0.246 g, 2.02 mmol), dicyclohexylcarbodiimide (DCC) (0.457 g, 2.22 mmol) and dimethylaminopyridine (DMAP) in catalytic amount (0.002 g, 0.2 mmol) in dry CH2Cl2 (DCM) (30 mL) was stirred at room temperature for 48 h.The white precipitate of DCUis obtained which was isolated by filtration and discarded, while the filtrate was evaporated to dryness. The resultant crude residue was purified by column chromatography on silica gel eluting with dichloromethane: methanol, recrystallization from methanol: chloroform (2:3) until constant transition temperatures were observed [43].
  • 68
  • [ 5438-19-7 ]
  • [ 130581-21-4 ]
  • C25H21ClO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h;
  • 69
  • [ 5438-19-7 ]
  • 4-hydroxy benzoyloxy naphthyl azo 4-pentyloxy benzene [ No CAS ]
  • C31H32N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h;
  • 70
  • [ 5438-19-7 ]
  • 1-(3-hydroxyphenyl)-3-(4-(octadecyloxy)phenyl)prop-2-en-1-one [ No CAS ]
  • C43H58O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 48h; General procedure for the synthesis of α-3-(4'-n-alkoxy benzoyloxy)benzoyl-β-4''-octadecyloxy phenyl ethylene (series-2) General procedure: The chalconyl ester based compound which had been prepared by the esterification of the appropriate 4-n-alkoxy benzoic acid (A) (2.02 mmol) and chalcone (C) (0.246 g, 2.02 mmol),dicyclohexylcarbodiimide (DCC) (0.457 g, 2.22mmol) and dimethylaminopyridine (DMAP)in catalytic amount (0.002 g, 0.2 mmol) in dry CH2Cl2 (DCM) (30 mL) was stirred at room temperature for 48 hr. The white precipitate of DCU is obtained, which was isolated by filtration and discarded, while the filtrate was evaporated to dryness. The resultant crude residue was purified by column chromatography on silica gel eluting with dichloromethane,recrystallization frommethanol: chloroform(2:3) until constant transition temperatures were observed
  • 71
  • [ 5438-19-7 ]
  • C29H32N4O4 [ No CAS ]
  • benzyl (1-(3-phenylpropyl)-5-(4-propoxybenzamido)-1H-benzo[d]imidazol-2-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% Stage #1: C29H32N4O4 With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: 4-propoxybenzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 16h; Inert atmosphere;
  • 72
  • [ 5438-19-7 ]
  • α-4-hydroxy phenyl β-4'-iodo benzoylethylene [ No CAS ]
  • C25H21IO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 48h; 2.3.3. synthesis of ester derivatives (C) General procedure: The compound has been prepared by esterification of the appropriate 4-n-alkoxy benzoic acid(A) (2.02 mmol) and chalcone (B) (0.246 g, 2.02 mmol), dicyclohexylcarbodiimide (DCC)(0.457 g, 2.22 mmol) and dimethylaminopyridine (DMAP) in catalytic amount (0.002 g,0.2 mmol) in dry CH2Cl2 (DCM) (30 mL) was stirred at room temperature for 48 h. The slightly observed white precipitate of dicyclohexyl urea is obtained which was isolated by filtration and removed, while the filtrate was evaporated to dryness. The resultant crude residue was purified by column chromatography on silica gel eluting with ethyl acetate: hexane (3:2)[54].
  • 73
  • [ 5438-19-7 ]
  • C24H19NO2 [ No CAS ]
  • C34H29NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 48h; 2.2.5 General procedure for the synthesis of (Series-1) General procedure: The compound has been prepared by esterification of the appropriate 4-n-alkoxy benzoic acid (1a) (2.02 mmol) and chalcone (4a) (0.246g, 2.02 mmol), dicyclohexyl carbodiimide(DCC) (0.457g, 2.22 mmol) and dimethylaminopyridine (DMAP) in catalytic amount(0.002g, 0.2 mmol) in dry CH2Cl2 (DCM) (30 mL) was stirred at room temperature for 48h. The slightly white precipitate of DCU is obtained which was isolated by filtration and remove, while the filtrate was evaporated to dryness. The resultant crude residue was purified by column chromatography on silica gel eluting with methanol: chloroformas eluent (1:4)
  • 74
  • [ 5438-19-7 ]
  • [ 99-76-3 ]
  • C18H18O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 48h; Synthesis of 4-(methoxy carbonyl) phenyl 4'-n-alkoxy benzoate (b) General procedure: 4-(methoxycarbonyl)phenyl 4-n-alkoxy benzoate has been prepared by esterification of the appropriate 4-n-alkoxy benzoic acid (2a) (2.02 mmol) and methyl-4-hydroxy benzoate (3a) (0.246 g, 2.02 mmol); dicyclohexyl carbodiimide (DCC) (0.457 g, 2.22 mmol) and dimethylaminopyridine (DMAP) in catalytic amount (0.002 g, 0.2 mmol) in dry CH2Cl2 (DCM) (60ml)was stirred at room temperature for 48 hr. The white precipitate of DCU was obtained which was isolated by filtration and removed, while the filtrate was evaporated to dryness. The resultant crude residue was purified by column chromatography on silica gel eluting with methanol : chloroform as eluent (2:4) [28].
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 48h; 2.2.3. Synthesis of 4-(methoxy carbonyl) phenyl 4’-n-alkoxy benzoate (3a) General procedure: 4-(methoxy carbonyl) phenyl 4’-n-alkoxy benzoate has been prepared by esterification of theappropriate 4-n-alkoxy benzoic acid (2a) (2.02 mmol) and methyl-4-hydroxy benzoate (3a)(2.02 mmol), dicyclohexyl carbodiimide (DCC) (2.22 mmol) and dimethylaminopyridine(DMAP) in catalytic amount (0.2 mmol) in dry CH2Cl2 (DCM) (60 ml) was stirred at roomtemperature for 48 h. The white precipitate of DCU is obtained which was isolated by filtrationand remove, while the filtrate was evaporated to dryness. The resultant crude residue waspurified by column chromatography on silica gel eluting withmethanol: chloroformas eluent(2:4) [43].
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; 2.2.3. Synthesis of 4-(Methoxy carbonyl) phenyl 4'-n-alkoxy benzoate (D) General procedure: 4-(methoxy carbonyl) phenyl 4'-n-alkoxy benzoate has been prepared by esterification of the appropriate 4-n-alkoxy benzoic acid (C) (2.02 mmol) and methyl-4-hydroxybenzoate (A) (2.02 mmol), dicyclohexyl carbodiimide (DCC) (2.22 mmol) and dimethylaminopyridine (DMAP) in catalytic amount (0.2 mmol) in dry CH2Cl2 (DCM) (60 ml) was stirred at room temperature for 48 h. The white precipitate of DCU is obtained which was isolated by filtration and remove, while the filtrate was evaporated to dryness. The resultant crude residue was purified by column chromatography on silica gel eluting with methanol: chloroform as eluent (2:4).
  • 75
  • [ 5438-19-7 ]
  • [ 159411-40-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 48 h / 20 °C 2: ethanol; water / Alkaline conditions; Reflux
Multi-step reaction with 2 steps 1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 48 h / 20 °C 2: potassium hydroxide / ethanol; water / Reflux
Multi-step reaction with 2 steps 1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 20 °C 2: ethanol / Reflux
  • 76
  • [ 5438-19-7 ]
  • [ 1033125-88-0 ]
  • C29H34N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h;
  • 77
  • [ 5438-19-7 ]
  • (E)-4-(3-(4-hydroxy phenyl)-3-oxoprop-1-en-1-yl)phenyl dodecanoate [ No CAS ]
  • C37H44O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; General procedure for the synthesis of final target compounds (C) General procedure: The final target compounds (C) has been prepared by esterification of the appropriate compound(3c) (2 mmol) and compound (2a) (2 mmol), dicyclohexyl carbodiimide (DCC) (2.22mmol) and dimethylaminopyridine (DMAP) in catalytic amount (0.2 mmol) in dry CH2Cl2(DCM) (30 ml) was stirred at room temperature for 28 h. The slightly yellowish precipitateof DCU is obtained which was isolated by filtration and remove, while the filtrate was evaporatedto dryness. The resultant crude residue was purified by column chromatography onsilica gel eluting with ethyl acetate: hexane as eluent (3:2) [48]. The characterization data oftarget compounds mention in supporting information. The synthesis route of target compoundswas mention in below Scheme 1.
  • 78
  • [ 5438-19-7 ]
  • 4'-(4-menthyloxy-4-oxobutanoyloxy)-4-hydroxybiphenyl [ No CAS ]
  • C36H42O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% With dmap; dicyclohexyl-carbodiimide In chloroform at 20℃; for 48h;
  • 79
  • [ 5438-19-7 ]
  • (E)-1-(3,4-bis(octadecyloxy)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one [ No CAS ]
  • C61H94O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; 2.3.4. Synthesis of ester derivatives (C) General procedure: The compound has been prepared by esterification of the appropriate 4-n-alkoxy benzoic acid(C) (2.02 mmol) and chalcone (B) (0.246 g, 2.02 mmol), dicyclohexyl carbodiimide (DCC)(0.457 g, 2.22 mmol) and dimethyl amino pyridine (DMAP) in catalytic amount (0.002 g, 0.2mmol) in dry CH2Cl2 (DCM) (30 mL) was stirred at room temperature for 12 h. The slightlyobserved off white yellow precipitate of dicyclohexyl urea is obtained which was isolated byfiltration and removed, while the filtrate was evaporated by using rota evaporator. The resultantcrude residue was purified by column chromatography on silica gel eluting with Ethylacetate: Hexane (3:2) [39].
  • 81
  • [ 261179-38-8 ]
  • [ 5438-19-7 ]
  • methyl (2R,3R)-7-methoxy-5-[(E)-3-methoxy-3-oxoprop-1-enyl]-2-[3-methoxy-4-(4-propoxybenzoyl)oxyphenyl]-2,3-dihydrobenzofuran-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With pyridine; dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; General method of synthesis General procedure: To a stirred solution of methyl (2R, 3R)-2-(4-hydroxy-3-methoxy-phenyl)-7-methoxy-5-[(E)-3-methoxy-3-oxo-prop-1-enyl]-2,3-dihydrobenzofuran-3-carboxylate [3] (1 eq.) in dichloromethane (30 ml) was added pyridine [7] (0.5 eq.), DMAP [6] (0.05 eq.), DCC [5] (1.3 eq.) and aromatic/substituted aromatic acids [4(a-h)] (1.3eq) respectively at room temp and stirredit for next 24 hrs. As the reaction proceeds the byproduct urea derivative precipitated out. The reaction mixture was filtered through celite bed which get rids of by product and the mother liquor on concentration yielded the pure final product in a quantitative yield.
  • 82
  • [ 5438-19-7 ]
  • (E)-3-(3,4-dibutoxyphenyl)-1-(4-hydroxy phenyl)prop-2-en-1-one [ No CAS ]
  • C33H38O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; 2.2.6 General procedure for the synthesis of final target compounds (2C) General procedure: The final target compounds (2C) has been prepared by esterification of the appropriatecompound (1c) (2 mmol) and compound (2b) (2 mmol), dicyclohexyl carbodiimide(DCC) (2.22 mmol) and dimethylaminopyridine (DMAP) in catalytic amount(0.2 mmol) in dry CH2Cl2 (DCM) (30 ml) was stirred at room temperature for 28 h. Theslightly yellowish precipitate of DCU is obtained which was isolated by filtration andremove, while the filtrate was evaporated to dryness. The resultant crude residue was purified by column chromatography on silica gel eluting with ethyl acetate: hexane aseluent
  • 83
  • [ 5438-19-7 ]
  • (E)-3-(3,4-dibutoxy-5-nitrophenyl)-1-(4-hydroxy phenyl)prop-2-en-1-one [ No CAS ]
  • C33H37NO8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; 2.2.7 General procedure for the synthesis of final target compounds (3C) General procedure: The final target compounds (3C) has been prepared by esterification of the appropriatecompound (3b) (2 mmol) and compound (1c) (2 mmol), dicyclohexyl carbodiimide(DCC) (2.22 mmol) and dimethylaminopyridine (DMAP) in catalytic amount(0.2 mmol) in dry CH2Cl2 (DCM) (30 ml) was stirred at room temperature for 28 h. Theslightly yellowish precipitate of DCU is obtained which was isolated by filtration andremove, while the filtrate was evaporated to dryness. The resultant crude residue waspurified by column chromatography on silica gel eluting with ethyl acetate: hexane aseluent (3:2)
  • 84
  • [ 5438-19-7 ]
  • (E)-4-(3-(4-hydroxyphenyl)-3-oxoprop-1-en-1-yl)phenyl tetradecanoate [ No CAS ]
  • C39H48O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h;
  • 85
  • [ 5438-19-7 ]
  • (E)-3-(4-(dimethylamino)phenyl)-1-(4-hydroxy-3-nitrophenyl)prop-2-en-1-one [ No CAS ]
  • C27H26N2O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h;
  • 86
  • [ 667-27-6 ]
  • [ 5438-19-7 ]
  • C13H16O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With 1,4-diaza-bicyclo[2.2.2]octane; palladium diacetate; copper(II) acetate monohydrate at 100℃; for 24h; Sealed tube;
  • 87
  • [ 1450-72-2 ]
  • [ 5438-19-7 ]
  • 4-propoxybenzoic acid 2-acetyl-4-methylphenyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% Stage #1: 5-methyl-2-hydroxyacetophenone; 4-propoxybenzoic acid With pyridine at 20℃; for 0.166667h; Stage #2: With trichlorophosphate at 0 - 10℃; for 3h; Synthesis of 4-Propoxy-benzoic acid 2-acetyl-4-methyl-phenyl ester (c’) At room temperature, equimolar 1-(2-Hydroxy-5-methyl-phenyl)-ethanone and 4-Propoxy-benzoic acid is dissolved in solvent pyridine and stirred for 10 min. using magnetic stirrer. Then to maintain the temperature of the reaction mixture to 0°C. In this mixture POCl3 added drop by drop with constant stirring, the temperature of the reaction mixture maintains below 10°C. After complete addition of POCl3, the mixture blend for 3 hours with the help of magnetic stirrer. The growth of process is tested by TL Chromatography and then the blend is kept whole night at normal temperature. Then the blend is added slowly on small mashed ice and if necessary acidulent using 1M HCl. The output of the reaction is filtered and it is washed using water and the creation is re-purified using ethyl alcohol. The purity of the compound is tested by TLC. The yield of the product (c’) is 81%. m. p. 94°C.
  • 88
  • [ 5438-19-7 ]
  • [ 100-83-4 ]
  • 3-formylphenyl 4-propoxybenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
90.1% Stage #1: 4-propoxybenzoic acid; meta-hydroxybenzaldehyde With dmap 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.
  • 89
  • [ 3315-19-3 ]
  • [ 5438-19-7 ]
  • 4-(benzo[d]oxazol-2-yl)phenyl 4-propoxybenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
67.2% Stage #1: 4-propoxybenzoic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 0.25h; Stage #2: 2-(4-hydroxyphenyl)benzoxazole In tetrahydrofuran at 20℃; for 3h; 4.3.71 4-(Benzo[d]oxazol-2-yl)phenyl 4-propoxybenzoate (14c) To a stirred solution of 4-propoxybenzoic acid (0.085g, 0.47mmol) in THF, DMAP (0.005g, 0.047mmol) and EDC.HCl (0.118g, 0.62mmol) were added and stirred at room temperature for 15min. Then 13 (0.1g, 0.47mmol) was added and stirred for 3h at room temperature. After completion of reaction (TLC), volatiles evaporated and the crude mass was partitioned between ethyl acetate and 10% sodium bicarbonate solution (2 times). Combined organic layer was washed with water and brine. Dried over sodium sulfate and purified by column chromatography (silica gel 100-200 mesh) using 15% ethyl acetate in hexanes. Yield: 0.118g, 67.2%, white solid, m.p: 170-172°C, 1H NMR (300MHz, CDCl3): δ 1.08 (t, J=7.5Hz, 3H), 1.87 (sextet, J=7.5Hz, 2H), 4.03 (t, J=6.6Hz, 2H), 7.00 (td, J=1.8, 4.8Hz, 2H), 7.36-7.39 (m, 2H), 7.41 (dd, J=0.9, 4.8Hz, 1H), 7.57-7.62 (m, 2H), 7.75-7.81 (m, 1H), 8.13 (t, J=1.8Hz, 1H), 8.17 (td, J=1.8,5.1Hz, 3H). 13C NMR (75MHz, CDCl3): δ 10.5, 22.5, 69.8, 110.6, 114.4, 120.0, 121.1, 122.5, 124.7, 125.2, 129.0, 132.4, 142.1, 150.8, 153.7, 162.5, 163.8, 164.5. HRMS (ESI) m/z calculated for C23H20NO4 (M+H)+: 374.1392; found: 374.1395.
  • 90
  • [ 3164-06-5 ]
  • [ 5438-19-7 ]
  • 3-(benzo[d]oxazol-2-yl)phenyl 4-propoxybenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% Stage #1: 4-propoxybenzoic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 0.25h; Stage #2: 2-(3-hydroxyphenyl)-1,3-benzoxazole In tetrahydrofuran at 20℃; for 3h; 4.3.85 3-(Benzo[d]oxazol-2-yl)phenyl 4-propoxybenzoate compound (18c) To a stirred solution of 4-propoxybenzoic acid (0.085 g, 0.47 mmol) in THF, DMAP (0.005 g, 0.047 mmol) and EDC.HCl (0.118 g, 0.62 mmol) were added and stirred at room temperature for 15 min. Then 17 (0.1 g, 0.47 mmol) was added and stirred for 3 h at room temperature. After completion of reaction (TLC), volatiles evaporated and the crude mass was partitioned between ethyl acetate and 10% sodium bicarbonate solution (2 times). Combined organic layer was washed with water and brine. Dried over sodium sulfate and purified by column chromatography (silica gel 100-200 mesh) using 15% ethyl acetate in hexanes. Yield: 0.139 g, 79.0%, white solid, m.p: 116-118 °C, 1H NMR (300 MHz, CDCl3): δ 1.08 (t, J = 7.5 Hz, 3H), 1.83 (sextet, J = 7.2 Hz, 2H), 4.03 (t, J = 6.6 Hz, 2H), 6.98-7.03 (m, 2ArH), 7.34-7.38 (m, 2ArH), 7.39-7.43 (m, 1ArH), 7.57-7.59 (m, 1ArH), 7.60-7.62 (m, 1ArH), 7.75-7.81 (m, 1ArH), 8.13 (t, J = 1.8 Hz, 1ArH), 8.15-8.20 (m, 3ArH). 13C NMR (75 MHz, CDCl3): δ 10.5, 22.5, 69.8, 110.7, 114.4, 120.2, 121.2, 124.7, 124.9, 125.1, 125.4, 128.6, 130.1, 132.4, 142.0, 150.8, 151.5, 162.2, 163.7, 164.7.HRMS (ESI) m/z calculated for C23H20NO4 (M+H)+: 374.1392; found: 374.1393.
  • 91
  • [ 5736-85-6 ]
  • [ 5438-19-7 ]
YieldReaction ConditionsOperation in experiment
89% Stage #1: 4-propoxybenzaldehyde In water; acetonitrile at 5℃; for 0.25h; Stage #2: With potassium permanganate In water; acetonitrile at 20℃; for 2h; Synthesis of 4-Propoxybenzoic acid (19): 4-Propoxybenzaldehyde (0.5 g, 3.04 mmol) was stirred in a mixture of Acetonitrile and water (1:1). To that Sodium phosphate dibasic (0.519 g, 3.65 mmol) was added and stirred at 5 °C for 15 minutes and then potassium permanganate (0.577 g, 3.65 mmol) was added in 3 lots. After 2 hours stirring at room temperature, volatiles were evaporated and dissolved in ethyl acetate and filtered through celite. The organic layer separated and washed with water and brine. It was dried over sodium sulfate and evaporated to give the carboxylic acid. Yield: 0.481 g, 89.0%, white solid, m.p: 132-134 °C, 1H NMR (400 MHz, CDCl3): δ 1.10 (t, J = 6.4 Hz, 3H), 1.89 (sextet, J = 6.8 Hz, 2H), 4.03 (t, J = 6.4 Hz, 2H), 6.98 (d, J = 6.8 Hz, 2ArH), 8.10 (d, J = 6.8 Hz, 2ArH), 9.96 (bs, 1H COOH). HRMS (ESI+): m/z calculated for C10H13O3 [M+H]+: 181.0864; found: 181.0865.
With potassium permanganate; sodium dihydrogenphosphate; ammonium cerium (IV) nitrate In water at 20℃; for 3h;
  • 92
  • [ 123-08-0 ]
  • [ 5438-19-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 80 °C 2: potassium permanganate; sodium dihydrogenphosphate; ammonium cerium (IV) nitrate / water / 3 h / 20 °C
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 8 h / 80 °C 2.1: sodium phosphate / acetonitrile; water / 0.25 h / 5 °C 2.2: 2 h / 20 °C
  • 93
  • [ 593-71-5 ]
  • [ 5438-19-7 ]
  • chloromethyl 4-propoxybenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
46.63% With triethylamine In N,N-dimethyl-formamide at 20℃; for 5h;
  • 94
  • [ 5438-19-7 ]
  • [ 627-30-5 ]
  • 3-chloropropyl 4-propoxybenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
76.2% Stage #1: 4-propoxybenzoic acid; 1-chloro-3-hydroxypropane With dmap In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 6h; Synthesis of 3-chloropropyl 4-propoxybenzoate (29): The carboxylic acid (19, 0.30 g, 1.66 mmol) was dissolved in DMF and stirred at room temperature. To that DMAP (0.02 g, 0.17 mmol) and 3-chloro-1-propanol (0.153 mL, 1.83 mmol) were added and stirred for 10 minutes. Then a DMF solution of DCC (0.41 g, 1.99 mmol) was added drop wise. Stirred at room temperature for 6 hours. After reaction completion by TLC, reaction mass diluted with ethyl acetate and the precipitate formed was filtered through celite bed. The ethyl acetate fraction was washed with 10% sodium bicarbonate followed by water and brine. It was dried over sodium sulfate and evaporated. The crude was purified by column chromatography using silica gel (100-200 mesh) and ethyl acetate in hexanes. Yield: 0.32 g, 76.2%, colorless liquid, 1H NMR (400 MHz, CDCl3): δ 1.05 (t, J = 7.2 Hz, 3H), 1.83 (sextet, J = 7.2 Hz, 2H), 2.23 (quintet, J = 6.4 Hz, 2H), 3.70 (t, J = 6.8 Hz, 2H), 3.98 (t, J = 6.4 Hz, 2H), 4.44 (t, J = 6.0 Hz, 2H), 6.91 (d, J = 8.8 Hz, 2ArH), 7.97 (d, J = 8.8 Hz, 2ArH). HRMS (ESI+): m/z calculated for C13H18ClO3 [M+H]+: 257.0944; found: 257.0945.
  • 95
  • [ 5438-19-7 ]
  • 4-[((5-(4-nitrophenyl)furan-2-yl)methylene)amino]phenol [ No CAS ]
  • 4-[((5-(4-nitrophenyl)furan-2-yl)methylene)amino]phenyl 4-propoxybenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With dmap; dicyclohexyl-carbodiimide In dichloromethane at 25℃; for 168h; 2.2.3. General procedure for synthesis of 4-[((5-(4-nitrophenyl)furan-2-yl)methylene)amino]phenyl 4-alkoxybenzoate (Ca-k) General procedure: The general procedure for the synthesis of the titled esters wasreported in our previous work with slight modifications [33,34]. Ina 100 mL round-bottom flask, furanimine phenol (B) (1.00 g,0.003 mol) and various 4-alkoxycarboxylic acids (Xn) (0.003 mol)were dissolved in dry dichloromethane (DCM) (100 mL). The esterificationcoupling reagents, N,N-dicyclohexylcarbodiimide (DCC) (0.66 g,0.003 mol) and 4-(Dimethylamino)pyridine (DMAP) (0.36 g,0.003 mol), were added to the reactants and then left in the flask at approximately25 °C to stir for one week. The precipitate formed (1,3-Dicyclohexyl urea DCU) was removed by filtration, and the filtratewas transferred to a separating funnel for the purification process. Itwas then washed with a dilute solution of acetic acid (5%, 80 mL) andthen with distilled water (80 mL). The separated organic layer wasdriedwith anhydrousmagnesiumsulfate; then theDCMsolventwas removedunder reduced pressure. The resulted crude products (Ca-k)wererecrystallized using ethanol.
  • 96
  • [ 5438-19-7 ]
  • 1-(2-aminoethyl)-3-((4-methoxybenzyl)oxy)-2-methylpyridin-4(1H)-one [ No CAS ]
  • C26H30N2O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% Stage #1: 4-propoxybenzoic acid With dmap; 2-mercaptothiazoline; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Stage #2: 1-(2-aminoethyl)-3-((4-methoxybenzyl)oxy)-2-methylpyridin-4(1H)-one In dichloromethane at 20℃; for 24h; 9 Add 4-propoxybenzoic acid (0.180g, 1mmol), dichloromethane (10mL) into a 100mL single-necked flask, and then add dicyclohexylcarbodiimide (0.226g, 1.1mmol), 2-mercaptothiazoline in sequence (0.130g, 1.1mmol), 4-dimethylaminopyridine (5mg, 0.04mmol), react at room temperature for 24h, after the reaction is over, filter, and concentrate the filtrate for use. Add 1-(2-aminoethyl)-2-methyl-3-methoxypyridin-4-one (0.182g, 1mmol) and dichloromethane (10mL) into a 100mL single-neck flask, and add the above filtrate dropwise, React at room temperature for 24 hours. After the reaction is complete, the reaction solution is concentrated and purified by silica gel column chromatography (dichloromethane: methanol = 100:1-20:1 gradient elution) to obtain a pale yellow solid (0.292 g) with a yield of 65%.
Stage #1: 4-propoxybenzoic acid With dmap; 2-mercaptothiazoline; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; Stage #2: 1-(2-aminoethyl)-3-((4-methoxybenzyl)oxy)-2-methylpyridin-4(1H)-one In dichloromethane at 20℃; for 24h;
  • 97
  • [ 5438-19-7 ]
  • (E)-7-hydroxy-3-(3-(4-hydroxyphenyl)acryloyl)–2H-chromen-2-one [ No CAS ]
  • (E)-4-(3-(7-((4-(propoxy)benzoyl)oxy)-2-oxo-2H-chromen-3-yl)-3-oxoprop-1-en-1-yl)phenyl 4-(propoxy)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% Stage #1: 4-propoxybenzoic acid With benzotriazol-1-ol; triethylamine In dichloromethane; 1,2-dichloro-ethane at 0 - 5℃; Stage #2: (E)-7-hydroxy-3-(3-(4-hydroxyphenyl)acryloyl)–2H-chromen-2-one In dichloromethane at 0 - 5℃; for 0.5h; Stage #3: In dichloromethane at 20℃; for 20h; 4.2.4. Synthesis of bis-ester coumarin chalcone derivatives 11a-m General procedure: To the solution of 4-alkoxy benzoic acid 8a-m (1.30 mmol,2.0 eq) in DCM (25 mL) was added EDC (0.37 g, 1.95 mmol,3.0 eq), HOBt (0.17 g, 1.30 mmol, 2.0 eq) followed by addition ofTEA (0.27 mL, 1.95 mmol, 3.0 eq). The resulting solution was stirred at 0-5 C for 10-15 min. To this cold reaction mixture, compound10(0.20 g, 0.65 mmol, 1.0 eq) was added and stirred for30 min at 0-5 C and then at room temperature for 20 h. The completionof reaction was checked by TLC. After completion of reaction,the reaction mixture was diluted with water (30 mL) andextracted with DCM (3 20 mL). The organic layer was separated,washed with water (20 mL), brine solution (20 mL), dried overanhydrous Na2SO4, filtered and concentrated on a rotavapor to giveresidue. The residue was scratched in methanol, filtered and driedto give compound 11a-m as yellow solid.
  • 98
  • [ 5438-19-7 ]
  • 1-(4-hydroxy-3-nitrophenyl)-3-(4-(iodo)phenyl)prop-2-en-1-one [ No CAS ]
  • C25H20INO6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 48h; 2.3.3. Synthesis of ester derivatives (Series-A) General procedure: The compound has been prepared by esterification of the appropriate 4-n-alkoxy benzoicacid (A) (1.0 mmol) and chalcone (B) (1.02 mmol), dicyclohexylcarbodiimide(DCC) (1.22 mmol) and dimethylaminopyridine (DMAP) in catalytic amount(0.2 mmol) in dry CH2Cl2 (DCM) (30 ml) was stirred at room temperature for 48 h. Thewhite precipitate of DCU is obtained which was isolated by filtration and discarded,while the filtrate was evaporated to dryness. The resultant crude residue was purified bycolumn chromatography on silica gel eluting with dichloromethane: methanol, recrystallizationfrom methanol: chloroform (2:3) until constant transition temperatures wereobserved [47].
  • 99
  • [ 5438-19-7 ]
  • 2-bromoethyl (E)-2-bromoethyl 3-(4-hydroxyphenyl)acrylate [ No CAS ]
  • C21H21BrO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h; 2.1.6. General method for the synthesis of (E)-4-(3-(2-bromoethoxy)-3-oxoprop-1-en-1-yl)phenyl 4-alkoxybenzoate (P1-P18) General procedure: To a stirred solution of 4-alkyloxybenzoic acid (A1-A18) (1 mmol) in dichloromethane(DCM) (5 mL) was added 2-bromoethyl (E)-2-bromoethyl 3-(4-hydroxyphenyl)acrylate(4a) (1.1 mmol). Further, N,N’-dicyclohexylcarbodiimide (DCC) (1.5 mmol) was addedto reaction mixture followed by 4-dimethylaminopyridine (DMAP) (0.05 mmol).Resulting solution stirred for 12-16 h at room temperature. After completion of the reactionmixture, reaction mixture was filtered, filtrate was concentrated under vacuum to give crudeproduct which was purified column chromatography to give (E)-4-(3-(2-bromoethoxy)-3-oxoprop-1-en-1-yl)phenyl 4-alkoxybenzoate (P1-P18) as white solid. All final compoundwas purified by column chromatography by 60-120 mesh silica. (Elutes in 0% to 20% ofEthyl acetate in Hexanes). TLC system (2:8, Ethyl acetate: Hexane).
  • 100
  • [ 5438-19-7 ]
  • (E)-2-methoxyethyl 3-(4-hydroxyphenyl)acrylate [ No CAS ]
  • C22H24O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h; 2.1.7. General method for the synthesis of (E)-4-(3-(2-methoxyethoxy)-3-oxoprop-1-en-1-yl)phenyl 4-alkoxybenzoate (V1-V18) General procedure: To a stirred solution of 4-alkyloxybenzoic acid (A1-A18) (1 mmol) in dichloromethane(DCM) (5 mL) was added (E)-2-methoxyethyl 3-(4-hydroxyphenyl)acrylate (4b)(1.1 mmol). Further, N,N’-dicyclohexylcarbodiimide (DCC) (1.5 mmol) was added to thereaction mixture followed by 4-dimethylaminopyridine (DMAP) (0.05 mmol). Theresulting solution stirred for 12-16 h at room temperature. After completion of the reactionmixture, the reaction mixture was filtered, the filtrate was concentrated under vacuumto give the crude product which was purified column chromatography to givetargeted molecules (V1-V18) as white solid.
  • 101
  • [ 5438-19-7 ]
  • (E)-2-(2-methoxyethoxy)ethyl 3-(4-hydroxyphenyl)acrylate [ No CAS ]
  • C24H28O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 15h; 2.1.8. General method for the synthesis of (E)-4-(3-(2-(2-methoxyethoxy)ethoxy)-3-oxoprop-1-en-1-yl)phenyl 4-alkoxybenzoate (M1-M18) General procedure: To a stirred solution of 4-alkyloxybenzoic acid (A1-A18) (1 mmol) in dichloromethane(DCM) (5 mL) was added (E)-2-(2-methoxyethoxy)ethyl 3-(4-hydroxyphenyl)acrylate(4c) (1.1 mmol). Further, N,N’-dicyclohexylcarbodiimide (DCC) (1.5 mmol) was addedto the reaction mixture followed by 4-dimethylaminopyridine (DMAP) (0.05 mmol).The resulting solution stirred for 12-16 h at room temperature. After completion of thereaction mixture, reaction mixture was filtered, the filtrate was concentrated under vacuumto give the crude product which was purified column chromatography to give targetedmolecules (M1-M18) as white solid.
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