Name: 5438-19-7|4-Propoxybenzoic acid|98%
Brand: Ambeed
SKU: A533547
Rating: 99 (28 reviews)

1
[ 622-85-5 ]
[ 463-72-9 ]
[ 5438-19-7 ]

Reference： [1]Chemische Berichte,1899,vol. 32,p. 1119
Justus Liebigs Annalen der Chemie,1888,vol. 244,p. 55

2
[ 5438-19-7 ]
[ 40782-58-9 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride
	With phosphorus pentachloride
	With thionyl chloride In benzene for 3h; Heating;

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

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[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]
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[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]
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[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]

3
[ 100256-94-8 ]
[ 5438-19-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide
	With potassium hydroxide
	With potassium hydroxide In ethanol

	Stage #1: 4-propoxy-benzoic acid ethyl ester With sodium hydroxide In ethanol at 20℃; for 3h; Stage #2: With hydrogenchloride; water In ethanol
	With ethanol; sodium hydroxide

Reference： [1]Pierce; Salsbury; Fredericksen [Journal of the American Chemical Society, 1942, vol. 64, p. 1691,1692] Cavill; Gibson [Journal of the Society of Chemical Industry, 1947, vol. 66, p. 274]
[2]Pierce; Salsbury; Fredericksen [Journal of the American Chemical Society, 1942, vol. 64, p. 1691,1692]
[3]Mundhe [Journal of the Indian Chemical Society, 1999, vol. 76, # 5, p. 246 - 249]
[4]Sit; Conway, Charles M.; Xie, Kai; Bertekap, Robert; Bourin, Clotilde; Burris, Kevin D. [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 3, p. 1272 - 1277]
[5]Gruzdev; Akopova; Frolova [Russian Journal of General Chemistry, 2013, vol. 83, # 4, p. 652 - 658][Zh. Obshch. Khim., 2013, vol. 83, # 4, p. 564 - 570,7]

4
[ 115478-59-6 ]
[ 5438-19-7 ]

Yield	Reaction Conditions	Operation 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;

Reference： [1]Periyasamy, Senthil; Subbiah, Selvaraj [Asian Journal of Chemistry, 2018, vol. 30, # 1, p. 85 - 88]
[2]Cohen; Dudley [Journal of the Chemical Society, 1910, vol. 97, p. 1747]
[3]Nakai; Konno; Kosuge; Sakuyama; Toda; Arai; Obata; Katsube; Miyamoto; Okegawa; Kawasaki [Journal of Medicinal Chemistry, 1988, vol. 31, # 1, p. 84 - 91]
[4]Sharma, Vinay S.; Patel, Sunil B.; Sharma, Anuj S.; Patel [Molecular Crystals and Liquid Crystals, 2017, vol. 656, # 1, p. 32 - 47]
[5]Sharma, Vinay S.; Sharma, Anuj S.; Jadeja, Upendra H.; Suthar, Deepak [Molecular Crystals and Liquid Crystals, 2018, vol. 665, # 1, p. 64 - 81]
[6]Sharma, Vinay S.; Suthar, Deepak; Sharma, Anuj S. [Molecular Crystals and Liquid Crystals, 2018, vol. 665, # 1, p. 100 - 118]
[7]Kashyap, Dinesh; Patel, Sunil; Prajapat, Varsha; Sharma, Vinay; Vasava, Dilip [Molecular Crystals and Liquid Crystals, 2019, vol. 681, # 1, p. 58 - 70]
[8]Shukla, Devendra K.; Sharma, Vinay S.; Prajapat, Varsha; Patel [Molecular Crystals and Liquid Crystals, 2019, vol. 682, # 1, p. 8 - 26]

5
[ 106-94-5 ]
[ 99-76-3 ]
[ 5438-19-7 ]

Yield	Reaction Conditions	Operation 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.

Reference： [1]Rohmann; Haas; Bergstermann [Archiv der Pharmazie, 1940, vol. 278, p. 425,434]
[2]Current Patent Assignee: OSAKA GAS CO LTD - US2003/211421, 2003, A1
[3]Buljan, Anđela; Knežević, Anamarija; Dokli, Irena; Lesac, Andreja [Croatica Chemica Acta, 2019, vol. 92, # 2, p. 173 - 179]

6
[ 106-94-5 ]
[ 99-96-7 ]
[ 5438-19-7 ]

Yield	Reaction Conditions	Operation 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 ]

Yield	Reaction Conditions	Operation in experiment
	With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine In dichloromethane for 1h; Ambient temperature;

Reference： [1]Ogawa; Yamamura; Miyamoto; Kondo; Yamashita; Nakaya; Chihara; Mori; Tominaga; Yabuuchi [Journal of Medicinal Chemistry, 1993, vol. 36, # 14, p. 2011 - 2017]

8
[ 5438-19-7 ]
[ 123-08-0 ]
[ 56800-28-3 ]

Yield	Reaction Conditions	Operation 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.

Reference： [1]Datta, Dhrubajyoti; Debnath, Joy; Franzblau, Scott G.; Ghosh, Kalyan Sundar; Hari, Natarajan; Ma, Rui; Rana, Shiwani; Velappan, Anand Babu [Bioorganic Chemistry, 2020, vol. 103]
[2]Matsunaga, Y.; Yuri, T. [Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1993, vol. 237, p. 145 - 150]
[3]Thaker; Patel, Pranay; Vansadia; Patel [Molecular Crystals and Liquid Crystals, 2007, vol. 466, # 1, p. 13 - 22]
[4]Thaker; Patel, Pranay [Molecular Crystals and Liquid Crystals, 2008, vol. 482, # 1, p. 3 - 20]
[5]Location in patent: experimental part Wei, Qiang; Yang, Huai; Wang, Yanbin [Molecular Crystals and Liquid Crystals, 2008, vol. 487, p. 31 - 38]
[6]Location in patent: experimental part Thaker; Patel; Dhimmar; Solnki; Chothani; Patel; Patel; Makavana [Molecular Crystals and Liquid Crystals, 2012, vol. 562, p. 98 - 113]
[7]Thaker; Chothani; Patel; Dhimmar; Solanki; Patel, Neeraj; Patel; Makawana [Molecular Crystals and Liquid Crystals, 2013, vol. 575, # 1, p. 64 - 76]
[8]Hagar, Mohamed A.; Katariya, Kanubhai D.; Nakum, Kiran J.; Soman, Shubhangi S.; Soni, Rina [Journal of Molecular Liquids, 2022, vol. 357]
[9]Hagaar, Mohamed; Katariya, Kanubhai D.; Nakum, Kiran J.; Soman, Shubhangi S.; Soni, Rina [Journal of Molecular Structure, 2022, vol. 1262]
[10]Hagar, Mohamed; Katariya, Kanubhai D.; Nakum, Kiran J. [Journal of Molecular Liquids, 2022, vol. 359]

9
[ 5438-19-7 ]
[ 95-01-2 ]
[ 177424-30-5 ]

Yield	Reaction Conditions	Operation 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;

Reference： [1]Bayle, J.-P.; Bui, E.; Perez, F.; Courtieu, J. [Bulletin de la Societe Chimique de France, 1989, # 4, p. 532 - 536]
[2]Thaker; Patel, Pranay; Vansadia; Patel [Molecular Crystals and Liquid Crystals, 2007, vol. 466, # 1, p. 13 - 22]
[3]Location in patent: experimental part Thaker; Patel, Pranay [Molecular Crystals and Liquid Crystals, 2009, vol. 509, # 1, p. 173 - 185]

10
[ 5438-19-7 ]
[ 848478-61-5 ]
4-(3-hydroxyoctanoyl)phenyl 4-propoxybenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 23h;

Reference： [1]Bezborodov; Kovganko [Russian Journal of Organic Chemistry, 2004, vol. 40, # 9, p. 1295 - 1299]

11
[ 5438-19-7 ]
[ 848478-63-7 ]
4-(3-chlorooctanoyl)phenyl 4-propoxybenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;

Reference： [1]Kovganko; Kovganko; Bezborodov [Russian Journal of Organic Chemistry, 2004, vol. 40, # 10, p. 1477 - 1482]

12
[ 27914-60-9 ]
[ 5438-19-7 ]
[ 99-96-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 82% 2: 3%	With potassium hydroxide In methanol at 20℃; for 10h;

Reference： [1]Ishizaki, Miyuki; Yamada, Makoto; Watanabe, Shin-Ichi; Hoshino, Osamu; Nishitani, Kiyoshi; Hayashida, Maiko; Tanaka, Atsuko; Hara, Hiroshi [Tetrahedron, 2004, vol. 60, # 36, p. 7973 - 7981]

13
[ 914784-11-5 ]
[ 5438-19-7 ]
4-(5-pentylisoxazol-3-yl)phenyl 4-propoxybenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With dmap; dicyclohexyl-carbodiimide In dichloromethane

Reference： [1]Kovganko; Kovganko [Russian Journal of Organic Chemistry, 2006, vol. 42, # 2, p. 243 - 248]

14
C₆₂H₉₂O₁₆ [ No CAS ]
[ 5438-19-7 ]
C₇₂H₁₀₂O₁₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With bis-2-propyl carbonate; 4-(dimethylamino)pyridinium tosylate In dichloromethane

Reference： [1]Lee; Cho; Kyo Jin Ihn; Lee; Oh; Zin [Journal of the American Chemical Society, 2001, vol. 123, # 19, p. 4647 - 4648]

15
C₉₂H₁₅₂O₂₆ [ No CAS ]
[ 5438-19-7 ]
C₁₀₂H₁₆₂O₂₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With bis-2-propyl carbonate; 4-(dimethylamino)pyridinium tosylate In dichloromethane

Reference： [1]Lee; Cho; Kyo Jin Ihn; Lee; Oh; Zin [Journal of the American Chemical Society, 2001, vol. 123, # 19, p. 4647 - 4648]

16
C₁₂₈H₂₂₄O₃₈ [ No CAS ]
[ 5438-19-7 ]
C₁₃₈H₂₃₄O₄₀ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With bis-2-propyl carbonate; 4-(dimethylamino)pyridinium tosylate In dichloromethane

Reference： [1]Lee; Cho; Kyo Jin Ihn; Lee; Oh; Zin [Journal of the American Chemical Society, 2001, vol. 123, # 19, p. 4647 - 4648]

17
[ 67-56-1 ]
[ 5438-19-7 ]
[ 115478-59-6 ]

Yield	Reaction Conditions	Operation 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;

Reference： [1]Masunari, Andrea; Tavares, Leoberto Costa [Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 12, p. 4229 - 4236]
[2]Location in patent: experimental part Ishii, Marina; Jorge, Salomão Dória; De Oliveira, Alex Alfredo; Palace-Berl, Fanny; Sonehara, Ieda Yuriko; Pasqualoto, Kerly Fernanda Mesquita; Tavares, Leoberto Costa [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 21, p. 6292 - 6301]
[3]Heimburg, Tino; Chakrabarti, Alokta; Lancelot, Julien; Marek, Martin; Melesina, Jelena; Hauser, Alexander-Thomas; Shaik, Tajith B.; Duclaud, Sylvie; Robaa, Dina; Erdmann, Frank; Schmidt, Matthias; Romier, Christophe; Pierce, Raymond J.; Jung, Manfred; Sippl, Wolfgang [Journal of Medicinal Chemistry, 2016, vol. 59, # 6, p. 2423 - 2435]

18
[ 5438-19-7 ]
[ 33905-61-2 ]

Yield	Reaction Conditions	Operation 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

Reference： [1]Mundhe [Journal of the Indian Chemical Society, 1999, vol. 76, # 5, p. 246 - 249]
[2]Deschenaux, Robert; Marendaz, Jean-Luc; Santiago, Julio [Helvetica Chimica Acta, 1993, vol. 76, # 2, p. 865 - 876]
[3]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]

19
[ 99-76-3 ]
[ 5438-19-7 ]

Yield	Reaction Conditions	Operation 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

Reference： [1]Nakai; Konno; Kosuge; Sakuyama; Toda; Arai; Obata; Katsube; Miyamoto; Okegawa; Kawasaki [Journal of Medicinal Chemistry, 1988, vol. 31, # 1, p. 84 - 91]
[2]Cohen; Dudley [Journal of the Chemical Society, 1910, vol. 97, p. 1747]
[3]Sharma, Vinay S.; Patel, Sunil B.; Sharma, Anuj S.; Patel [Molecular Crystals and Liquid Crystals, 2017, vol. 656, # 1, p. 32 - 47]
[4]Sharma, Vinay S.; Sharma, Anuj S.; Jadeja, Upendra H.; Suthar, Deepak [Molecular Crystals and Liquid Crystals, 2018, vol. 665, # 1, p. 64 - 81]
[5]Sharma, Vinay S.; Suthar, Deepak; Sharma, Anuj S. [Molecular Crystals and Liquid Crystals, 2018, vol. 665, # 1, p. 100 - 118]
[6]Kashyap, Dinesh; Patel, Sunil; Prajapat, Varsha; Sharma, Vinay; Vasava, Dilip [Molecular Crystals and Liquid Crystals, 2019, vol. 681, # 1, p. 58 - 70]
[7]Shukla, Devendra K.; Sharma, Vinay S.; Prajapat, Varsha; Patel [Molecular Crystals and Liquid Crystals, 2019, vol. 682, # 1, p. 8 - 26]

20
[ 120-47-8 ]
[ 5438-19-7 ]

Yield	Reaction Conditions	Operation 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

Reference： [1]Pierce; Salsbury; Fredericksen [Journal of the American Chemical Society, 1942, vol. 64, p. 1691,1692]
[2]Cavill; Gibson [Journal of the Society of Chemical Industry, 1947, vol. 66, p. 274]
[3]Gruzdev; Akopova; Frolova [Russian Journal of General Chemistry, 2013, vol. 83, # 4, p. 652 - 658][Zh. Obshch. Khim., 2013, vol. 83, # 4, p. 564 - 570,7]

21
[ 5438-19-7 ]
[ 64328-60-5 ]

Yield	Reaction Conditions	Operation 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].

Reference： [1]Claesen et al. [Journal of Pharmacy and Pharmacology, 1954, vol. 6, p. 127]
[2]Ishii, Marina; Jorge, Salomão Dória; De Oliveira, Alex Alfredo; Palace-Berl, Fanny; Sonehara, Ieda Yuriko; Pasqualoto, Kerly Fernanda Mesquita; Tavares, Leoberto Costa [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 21, p. 6292 - 6301]
[3]Jorge, Salomão Dória; Palace-Berl, Fanny; Mesquita Pasqualoto, Kerly Fernanda; Ishii, Marina; Ferreira, Adilson Kleber; Berra, Carolina Maria; Bosch, Rosemary Viola; Maria, Durvanei Augusto; Tavares, Leoberto Costa [European Journal of Medicinal Chemistry, 2013, vol. 64, p. 200 - 214]
[4]De Azevedo, Ricardo Alexandre; Ferreira, Adilson Kleber; Jorge, Salomo Dria; Palace-Berl, Fanny; Pasqualoto, Kerly Fernanda Mesquita; Silva, Marcelo Nunes; Tavares, Leoberto Costa; Teixeira, Sarah Fernandes; Zingales, Bianca; Zorzi, Rodrigo Rocha [European Journal of Medicinal Chemistry, 2015, vol. 96, p. 330 - 339]

22
[ 443682-63-1 ]
[ 5438-19-7 ]
(R)-4-(3-ethyl-1-methylpentyloxycarbonyl)phenyl-4-n-propyloxybenzoate [ No CAS ]

Yield	Reaction Conditions	Operation 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%).

Reference： [1]Current Patent Assignee: MITSUBISHI GAS CHEMICAL COMPANY INC - US6677475, 2004, B2 Location in patent: Page column 15

23
[ 4143-61-7 ]
[ 436848-04-3 ]
[ 5438-19-7 ]
[ 469858-99-9 ]

Yield	Reaction Conditions	Operation 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).

Reference： [1]Current Patent Assignee: OSAKA GAS CO LTD - US2003/211421, 2003, A1

24
[ 5438-19-7 ]
[ 369358-82-7 ]

Yield	Reaction Conditions	Operation 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).

Reference： [1]Current Patent Assignee: ABBVIE INC - US2002/2152, 2002, A1

25
[ 5438-19-7 ]
[ 369358-84-9 ]

Yield	Reaction Conditions	Operation 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).

Reference： [1]Current Patent Assignee: ABBVIE INC - US2002/2152, 2002, A1

26
[ 5438-19-7 ]
[ 369360-05-4 ]

Yield	Reaction Conditions	Operation 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).

Reference： [1]Current Patent Assignee: ABBVIE INC - US2002/2152, 2002, A1

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 ]

Yield	Reaction Conditions	Operation 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

Reference： [1]Current Patent Assignee: PFIZER INC - WO2006/100591, 2006, A1 Location in patent: Page/Page column 107

28
[ 67-56-1 ]
terbium(III) nitrate hexahydrate [ No CAS ]
[ 5438-19-7 ]
[Tb(4-ethoxybenzoate)2(NO₃)](CH₃OH)2]n [ No CAS ]

Yield	Reaction Conditions	Operation 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.;

Reference： [1]Lam, Alex Wai-Hing; Wong, Wing-Tak; Gao, Song; Wen, Gehui; Zhang, Xi-Xiang [European Journal of Inorganic Chemistry, 2003, # 1, p. 149 - 163]

29
[ 67-56-1 ]
gadolinium(III) nitrate hexahydrate [ No CAS ]
[ 5438-19-7 ]
[Gd(4-ethoxybenzoate)2(NO₃)](CH₃OH)2]n [ No CAS ]

Yield	Reaction Conditions	Operation 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.;

Reference： [1]Lam, Alex Wai-Hing; Wong, Wing-Tak; Gao, Song; Wen, Gehui; Zhang, Xi-Xiang [European Journal of Inorganic Chemistry, 2003, # 1, p. 149 - 163]

30
[ 67-56-1 ]
europium(III) nitrate hexahydrate [ No CAS ]
[ 5438-19-7 ]
[Eu(4-ethoxybenzoate)2(NO₃)](CH₃OH)2]n [ No CAS ]

Yield	Reaction Conditions	Operation 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.;

Reference： [1]Lam, Alex Wai-Hing; Wong, Wing-Tak; Gao, Song; Wen, Gehui; Zhang, Xi-Xiang [European Journal of Inorganic Chemistry, 2003, # 1, p. 149 - 163]

31
[ 99-96-7 ]
[ 5438-19-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium hydroxide In ethanol Heating;
	With potassium hydroxide In methanol
	With potassium hydroxide In methanol Reflux;

In methanol

32
[ 5438-19-7 ]
[ 32223-64-6 ]

Yield	Reaction Conditions	Operation in experiment
	With diphenyl phosphoryl azide; triethylamine In toluene at 20 - 105℃; for 1.16667h; Inert atmosphere;

Reference： [1]Sit; Conway, Charles M.; Xie, Kai; Bertekap, Robert; Bourin, Clotilde; Burris, Kevin D. [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 3, p. 1272 - 1277]

33
[ 4254-15-3 ]
[ 5438-19-7 ]
[ 1243060-59-4 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃;

Reference： [1]Location in patent: scheme or table Zhang, Hai Quan; Liu, Wen Ke; Zhao, Li Cheng; Huang, Wei; Zhang, Shuai; Li, Ying; Yang, Huai [Chinese Chemical Letters, 2010, vol. 21, # 2, p. 139 - 142]

34
[ 5438-19-7 ]
[ 128625-52-5 ]
[ 618-39-3 ]
[ 876179-80-5 ]
[ 1263815-73-1 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 1177 - 1179

35
[ 5438-19-7 ]
[ 124-42-5 ]
C₁₂H₁₆N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 25℃; for 2h;

Reference： [1]Castanedo, Georgette M.; Seng, Pamela S.; Blaquiere, Nicole; Trapp, Sean; Staben, Steven T. [Journal of Organic Chemistry, 2011, vol. 76, # 4, p. 1177 - 1179]

36
[ 5438-19-7 ]
[ 57297-29-7 ]
C₁₄H₁₈N₂O₂ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 1177 - 1179

37
[ 5438-19-7 ]
[ 618-39-3 ]
[ 1263815-73-1 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 25℃; for 2h;

Reference： [1]Castanedo, Georgette M.; Seng, Pamela S.; Blaquiere, Nicole; Trapp, Sean; Staben, Steven T. [Journal of Organic Chemistry, 2011, vol. 76, # 4, p. 1177 - 1179]

38
[ 5438-19-7 ]
[ 932042-48-3 ]

Yield	Reaction Conditions	Operation 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

Reference： [1]Kovganko; Kovganko; Polovkov [Russian Journal of Organic Chemistry, 2010, vol. 46, # 12, p. 1812 - 1816]
[2]Bai, Feifei; Fang, Jianguo; Song, Zi-Long; Zhang, Baoxin [Journal of Agricultural and Food Chemistry, 2020, vol. 68, # 7, p. 2214 - 2231]

39
[ 5438-19-7 ]
[ 104-42-7 ]
12A + (3BA)2 [ No CAS ]

Reference： [1]Molecular Crystals and Liquid Crystals,2010,vol. 524,p. 131 - 143

40
[ 5438-19-7 ]
[ 551-93-9 ]
[ 1319210-02-0 ]

Yield	Reaction Conditions	Operation in experiment
72%	With triethylamine In tetrahydrofuran at 70℃; for 3h;

Reference： [1]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]

41
1-benzyl piperazine dihydrobromide [ No CAS ]
[ 5438-19-7 ]
[ 617675-58-8 ]

Yield	Reaction Conditions	Operation 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.

Reference： [1]Dou, Dengfeng; He, Guijia; Mandadapu, Sivakoteswara Rao; Aravapalli, Sridhar; Kim, Yunjeong; Chang, Kyeong-Ok; Groutas, William C. [Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 1, p. 377 - 379]

42
[ 5438-19-7 ]
[ 1017029-32-1 ]
[ 1397262-86-0 ]

Yield	Reaction Conditions	Operation 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).

Reference： [1]Moussa, Iman A.; Banister, Samuel D.; Manoli, Miral; Doddareddy, Munikumar Reddy; Cui, Jinquan; MacH, Robert H.; Kassiou, Michael [Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 17, p. 5493 - 5497]

43
[ 99-96-7 ]
[ 5438-19-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide In methanol
	With potassium hydroxide In methanol Reflux;
	With potassium hydroxide In ethanol for 8h; Reflux;

In methanol

Reference： [1]Patel; Vyas; Doshi [Molecular Crystals and Liquid Crystals, 2012, vol. 569, # 1, p. 15 - 23]
[2]Khunt; Kotadiya; Bhoya [Molecular Crystals and Liquid Crystals, 2015, vol. 607, # 1, p. 32 - 40] Patel, H. Brijesh; Doshi [Molecular Crystals and Liquid Crystals, 2015, vol. 606, # 1, p. 56 - 65] Marathe; Doshi [Molecular Crystals and Liquid Crystals, 2016, vol. 625, # 1, p. 81 - 92]
[3]Kadam, Vinay S.; Shaikh, Saminaparwin G.; Patel, Arun L. [Journal of Molecular Structure, 2016, vol. 1114, p. 181 - 188]
[4]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, 2016, vol. 634, # 1, p. 41 - 49]

44
[ 99-96-7 ]
[ 5438-19-7 ]

Yield	Reaction Conditions	Operation 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;

Reference： [1]Chaudhari; Chauhan; Doshi [Molecular Crystals and Liquid Crystals, 2013, vol. 575, # 1, p. 88 - 95]
[2]Suthar; Doshi, Ankita A.; Doshi [Molecular Crystals and Liquid Crystals, 2013, vol. 574, # 1, p. 75 - 83]
[3]Sharma, Vinay S.; Patel, Sunil B.; Sharma, Anuj S.; Patel [Molecular Crystals and Liquid Crystals, 2017, vol. 656, # 1, p. 32 - 47]
[4]Sharma, Vinay S.; Sharma, Anuj S.; Jadeja, Upendra H.; Suthar, Deepak [Molecular Crystals and Liquid Crystals, 2018, vol. 665, # 1, p. 64 - 81]
[5]Sharma, Vinay S.; Suthar, Deepak; Sharma, Anuj S. [Molecular Crystals and Liquid Crystals, 2018, vol. 665, # 1, p. 100 - 118]
[6]Kashyap, Dinesh; Patel, Sunil; Prajapat, Varsha; Sharma, Vinay; Vasava, Dilip [Molecular Crystals and Liquid Crystals, 2019, vol. 681, # 1, p. 58 - 70]
[7]Shukla, Devendra K.; Sharma, Vinay S.; Prajapat, Varsha; Patel [Molecular Crystals and Liquid Crystals, 2019, vol. 682, # 1, p. 8 - 26]
[8]Buljan, Anđela; Knežević, Anamarija; Dokli, Irena; Lesac, Andreja [Croatica Chemica Acta, 2019, vol. 92, # 2, p. 173 - 179]
[9]Hagaar, Mohamed; Katariya, Kanubhai D.; Nakum, Kiran J.; Soman, Shubhangi S.; Soni, Rina [Journal of Molecular Structure, 2022, vol. 1262]

45
[ 102-71-6 ]
[ 5438-19-7 ]
[ 1440507-27-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: triethanolamine; 4-propoxybenzoic acid In chloroform for 0.166667h; Stage #2: With dmap; dicyclohexyl-carbodiimide In chloroform for 12h;

Reference： [1]Gruzdev; Akopova; Frolova [Russian Journal of General Chemistry, 2013, vol. 83, # 4, p. 652 - 658][Zh. Obshch. Khim., 2013, vol. 83, # 4, p. 564 - 570,7]

46
[ 5438-19-7 ]
potassium trans-hex-1-enyltrifluoroborate [ No CAS ]
[ 1440548-48-0 ]

Yield	Reaction Conditions	Operation in experiment
81%	With dmap; oxygen; copper(I) bromide In acetonitrile at 60℃; for 24h; Molecular sieve; stereospecific reaction;

Reference： [1]Huang, Fang; Quach, Tan D.; Batey, Robert A. [Organic Letters, 2013, vol. 15, # 12, p. 3150 - 3153]

47
[ 5438-19-7 ]
potassium trifluoro(prop-1-en-1-yl)borate [ No CAS ]
[ 1440548-71-9 ]

Yield	Reaction Conditions	Operation in experiment
71%	With dmap; oxygen; copper(I) bromide In acetonitrile at 60℃; for 24h; Molecular sieve; stereospecific reaction;

Reference： [1]Huang, Fang; Quach, Tan D.; Batey, Robert A. [Organic Letters, 2013, vol. 15, # 12, p. 3150 - 3153]

48
[ 5438-19-7 ]
[ 77103-47-0 ]
[ 1462352-06-2 ]

Yield	Reaction Conditions	Operation in experiment
73%	With dmap; dicyclohexyl-carbodiimide In dichloromethane for 25h;

Reference： [1]Kovganko; Kovganko [Russian Journal of General Chemistry, 2013, vol. 83, # 8, p. 1556 - 1562][Zh. Obshch. Khim., 2013, vol. 83, # 8, p. 1326 - 1333,8]

49
[ 123-91-1 ]
[ 5438-19-7 ]
[ 1597710-63-8 ]

Yield	Reaction Conditions	Operation in experiment
91%	With iron(III)-acetylacetonate; di-tert-butyl peroxide at 120℃; for 24h; Schlenk technique;

Reference： [1]Zhao, Jincan; Fang, Hong; Zhou, Wei; Han, Jianlin; Pan, Yi [Journal of Organic Chemistry, 2014, vol. 79, # 9, p. 3847 - 3855]

50
[ 5438-19-7 ]
C₆H₁₃N₂O₃Pol [ No CAS ]
C₁₆H₂₃N₂O₅Pol [ No CAS ]

Yield	Reaction Conditions	Operation 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).

Reference： [1]Hansen, Finn K.; Sumanadasa, Subathdrage D.M.; Stenzel, Katharina; Duffy, Sandra; Meister, Stephan; Marek, Linda; Schmetter, Rebekka; Kuna, Krystina; Hamacher, Alexandra; Mordmüller, Benjamin; Kassack, Matthias U.; Winzeler, Elizabeth A.; Avery, Vicky M.; Andrews, Katherine T.; Kurz, Thomas [European Journal of Medicinal Chemistry, 2014, vol. 82, p. 204 - 213]

51
[ 5438-19-7 ]
[ 79-19-6 ]
[ 299936-27-9 ]

Yield	Reaction Conditions	Operation 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.

Reference： [1]Al-Malki, Mustafa K.S.; Hameed, Ayad S.; Al-Dujaili, Ammar H. [Molecular Crystals and Liquid Crystals, 2014, vol. 593, # 1, p. 34 - 42]

52
[ 5438-19-7 ]
[ 500195-02-8 ]

Yield	Reaction Conditions	Operation 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

Reference： [1]De Azevedo, Ricardo Alexandre; Ferreira, Adilson Kleber; Jorge, Salomo Dria; Palace-Berl, Fanny; Pasqualoto, Kerly Fernanda Mesquita; Silva, Marcelo Nunes; Tavares, Leoberto Costa; Teixeira, Sarah Fernandes; Zingales, Bianca; Zorzi, Rodrigo Rocha [European Journal of Medicinal Chemistry, 2015, vol. 96, p. 330 - 339]

53
[ 5438-19-7 ]
[ 115914-43-7 ]
nonane-1,9-diyl bis(4,1-phenylene) bis(4-propoxybenzoate) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80.4%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane

Reference： [1]Mandle, Richard J.; Davis, Edward J.; Archbold, Craig T.; Voll, Constantin C. A.; Andrews, Jessica L.; Cowling, Stephen J.; Goodby, John W. [Chemistry - A European Journal, 2015, vol. 21, # 22, p. 8158 - 8167]

54
[ 5438-19-7 ]
[ 5424-02-2 ]
C₂₅H₂₁ClO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h;

Reference： [1]Khunt; Kotadiya; Bhoya [Molecular Crystals and Liquid Crystals, 2016, vol. 625, # 1, p. 20 - 29]

55
[ 97727-87-2 ]
[ 5438-19-7 ]
C₂₃H₂₀O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h;

Reference： [1]Maheta; Bhoya [Molecular Crystals and Liquid Crystals, 2016, vol. 625, # 1, p. 72 - 80]

56
[ 5438-19-7 ]
[ 88521-99-7 ]
C₂₆H₂₄O₄ [ No CAS ]

Yield	Reaction Conditions	Operation 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

Reference： [1]Kotadiya; Khunt; Bhoya [Molecular Crystals and Liquid Crystals, 2016, vol. 626, # 1, p. 45 - 57]

57
[ 97727-84-9 ]
[ 5438-19-7 ]
C₂₅H₂₁BrO₄ [ No CAS ]

Yield	Reaction Conditions	Operation 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.

Reference： [1]Khunt; Kotadiya; Bhoya [Molecular Crystals and Liquid Crystals, 2016, vol. 626, # 1, p. 31 - 44]

58
[ 5438-19-7 ]
α-(4-hydroxybenzoyl)-β-(2,5-dimethoxyphenyl)ethylene [ No CAS ]
C₂₇H₂₆O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h;

Reference： [1]Khunt; Kotadiya; Bhoya [Molecular Crystals and Liquid Crystals, 2016, vol. 626, # 1, p. 68 - 80]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	5438-19-7	MDL No. :	MFCD00013989
Formula :	C₁₀H₁₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GDFUWFOCYZZGQU-UHFFFAOYSA-N
M.W :	180.20 g/mol	Pubchem ID :	138500
Synonyms :

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:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
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P270	Do not eat, drink or smoke when using this product.
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P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
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P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
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P406	Store in corrosive resistant/ container with a resistant inner liner.
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P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
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H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 5438-19-7 ]

Quality Control of [ 5438-19-7 ]

Related Doc. of [ 5438-19-7 ]

Product Details of [ 5438-19-7 ]

Safety of [ 5438-19-7 ]

Application In Synthesis of [ 5438-19-7 ]

[ 5438-19-7 ] Synthesis Path-Downstream 1~58

Precautionary Statements-General

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Physical hazards

Health hazards

Environmental hazards

Inquiry