ChemicalBook CAS DataBase List 4-(5-(4-(pentyloxy)phenyl)isoxazol-3-yl)benzoic acid

4-(5-(4-(pentyloxy)phenyl)isoxazol-3-yl)benzoic acid synthesis

8synthesis methods

Product Name:4-(5-(4-(pentyloxy)phenyl)isoxazol-3-yl)benzoic acid
CAS Number:179162-55-1
Molecular formula:C21H21NO4
Molecular Weight:351.4

179162-64-2 Synthesis

179162-64-2
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4-(5-(4-(pentyloxy)phenyl)isoxazol-3-yl)benzoic acid

179162-55-1
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Yield:179162-55-1 92%

Reaction Conditions:

with sodium hydroxide in tetrahydrofuran;ethanol at 80 - 90; for 2 h;

Steps:

4-(5-(4-(pentyloxy)phenyl)isoxazol-3-yl)benzoicacid (4)

To a solution of 4-(5-(4-(pentyloxy)phenyl)isoxazol-3-yl)benzoate 12 (0.35 g, 0.095 mol) ) in ethanol (4.20 mL, 12 Vol) and THF (7.0 mL, 20 Vol), 2N sodium hydroxide solution (0.70 mL, 2 Vol) was added and the reaction mixture was refluxed at 80-90 °C for 2h. After completion of starting material, reaction mixture was cooled to room temperature, quenched with ice cold water and pH adjusted to 2.0 with 1N HCl. Obtained solid was filtered, washed with water and dried under vacuum to give 4-(5-(4-(pentyloxy)phenyl)isoxazol-3-yl)benzoicacid 4 (0.31 g, 92% yield) as a white solid. ¹H NMR (400 MHz, DMSO-d₆): δ 13.16 (s, 1H, COOH), 8.07 (d, J = 8.0 Hz, 2H, H-3 & H-3’), 8.00 (d, J = 8.4 Hz, 2H, H-4 & H-4’), 7.80 (d, J = 8.8 Hz, 2H, H-10 & H-10’), 7.47 (s, 1H, H-7), 7.06 (d, J = 8.8 Hz, 2H, H-11 & H-11’), 3.98 (t, J = 6.4 Hz, 2H, H-13), 1.71-1.67 (m, 2H, H-14), 1.38-1.28 (m, 4H, H-15 & H-16), 0.86 (t, J = 6.8 Hz, 3H, H-17); ¹³C NMR (100 MHz, DMSO-d₆); δ 170.6 (C-1), 167.2 (C-8), 162.2 (C-6), 160.8 (C-12), 133.0 (C-5), 132.5 (C-2), 130.4 (C-3 & C-3’), 127.7 (C-4 & C-4’), 127.1 (C-10 & C-10’), 119.6 (C-9), 115.5 (C-11 & C-11’), 97.6 (C-7), 68.1 (C-18), 28.6 (C-14), 28.0 (C-15), 22.2 (C-16), 14.2 (C-17); Mass (ESI) m/z = 352.0 [M+H]⁺.

References:

Rao, Pallavi;Hussain, Ismail;Rao, Venkataramanarao;Sen, Saikat;Oruganti, Srinivas [Synthetic Communications,2019,vol. 49,# 17,p. 2180 - 2187] Location in patent:supporting information

110-53-2 Synthesis