ChemicalBook CAS DataBase List 3,5-Dichlorobenzoic acid

3,5-Dichlorobenzoic acid synthesis

13synthesis methods

Product Name:3,5-Dichlorobenzoic acid
CAS Number:51-36-5
Molecular formula:C7H4Cl2O2
Molecular Weight:191.01

Synthesis of 3,5-dichlorobenzoic acid: 200 parts of ethanol is slowly added to a solution, heated to 70°C, of the diazonium salt prepared as described in Example 1 from 412 parts of 3,5-dichloroanthranilic acid; elimination of nitrogen immediately takes place with evolution of heat. The mixture is stirred for another 15 minutes and 350 parts (92% of theory) of 3,5-dichlorobenzoic acid having a melting point of 176° to 178°C is isolated as described in Example 1.

6575-00-4 Synthesis

6575-00-4
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51-36-5
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Yield:51-36-5 93%

Reaction Conditions:

with water;sodium hydroxide for 6 h;Reflux;

Steps:

Synthesis of 3,5-Dichlorobenzoic Acid (2)

To a solution of sodium hydroxide (2.9 g, 0.073 mol) in 10mL of deionized water, 3,5-dichlorobenzonitrile (1) (5 g,0.029 mol) was added slowly. Under stirring, the mixturewas heated and refluxed for 6 h. The reaction was monitoredby TLC (methanol/ethyl acetate: v/v = 1/4). After thereaction completed, the mixture was cooled to room temperatureand the pH value of the solution was adjusted to1-3 by hydrogen chloride aqueous (2 mol/L). A white solidprecipitated, which was filtered under reduced pressure,washed with water, and dried to give a white powder. Thefiltrate was extracted with ethyl acetate. The white powderobtained in two crops was recrystallized from deionizedwater to obtain 3,5-dichlorobenzoic acid (2). Yield: 5.1 g(93%). FT-IR (KBr disc, cm^-1): υ(C-H) 3084, υ(O-H) 2663,υ(C=O) 1706, υ(C-C) 1570 and 1448, β(C-O-H) 1403,β(C-H) 1289 and 1237, γ(C-H) 769. 1H NMR (400 MHz,DMSO-d6): δ(ppm) 7.90 (t, J = 2.0 Hz, 1H, Ph), 7.85 (d,J = 2.0 Hz, 2H, Ph).

References:

Zhang, Jun;Li, Yue;Wang, Bei;Jia, Ai-Quan;Zhang, Qian-Feng [Journal of Chemical Crystallography,2021,vol. 51,# 1,p. 108 - 115]