ChemicalBook CAS DataBase List 4-METHYL-2-NITROBENZOIC ACID

4-METHYL-2-NITROBENZOIC ACID synthesis

10synthesis methods

Product Name:4-METHYL-2-NITROBENZOIC ACID
CAS Number:27329-27-7
Molecular formula:C8H7NO4
Molecular Weight:181.15

89-58-7

27329-27-7

General procedure for the synthesis of 4-methyl-2-nitrobenzoic acid from 2,5-dimethylnitrobenzene: 1,4-dimethyl-2-nitrobenzene (907 mg, 6 mmol, 1.0 eq.) and sodium hydroxide (1.8 g, 45.0 mmol, 7.5 eq.) were added to a 100 mL autoclave with 10 mL of 80% (v/v) aqueous ethanol (8 mL of ethanol mixed with 2 mL of water). After oxygenation three times, oxygen was passed to a pressure of 1.8 MPa. The reaction was carried out in an oil bath at a controlled temperature of 65 °C for 24 h. After the reaction was completed, the reaction was diluted with methanol. After completion of the reaction, the reaction mixture was diluted with methanol and the pH was adjusted to 2-3. The solvent was removed by distillation under reduced pressure. Ethyl acetate was added for extraction and the organic phase was dried and filtered. The product was separated by column chromatography and 129 mg (0.85 mmol) of unreacted 1,4-dimethyl-2-nitrobenzene was recovered, giving 86% conversion of 1,4-dimethyl-2-nitrobenzene. The target product 4-methyl-2-nitrobenzoic acid 811 mg (4.48 mmol) was obtained in 75% yield.

89-58-7 Synthesis

89-58-7
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27329-27-7
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$7.00/250mg

Yield: 75%

Reaction Conditions:

with oxygen;sodium hydroxide in ethanol;water at 65; under 13501.4 Torr; for 24 h;Autoclave;Solvent;Concentration;

Steps:

2 Example 2:
1,4-dimethyl-2-nitrobenzene (907 mg, 6 mmol, 1.0 eq)Sodium hydroxide (1.8 g, 45.0 mmol, 7.5 eq)Was added to a 100 ml autoclave,10 ml of 80% (v / v) ethanol (8 ml of ethanol, 2 ml of water)After charging oxygen three times,Passing oxygen gas (pressure 1.8MPa),In the oil bath temperature control 65 for 24 hoursAfter the reaction was diluted with methanol,Neutral and PH = 2-3,The solvent was removed under reduced pressure,After adding ethyl acetate, the mixture was dried and filtered.Separated by chromatography,1,4-dimethyl-2-nitrobenzene recovered 129mg (0.85mmol),The conversion of 1,4-dimethyl-2-nitrobenzene was 86%4-methyl-2-nitrobenzoic acid was obtained811 mg (4.48 mmol) in 75% yield

References:

Zhejiang University of Technology;She Yuanbin;Li Guijie;Fang Kun CN106995374, 2017, A Location in patent:Paragraph 0031; 0032; 0033; 0034; 0035; 0036; 0037-0042

5326-39-6 Synthesis