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