ChemicalBook CAS DataBase List AURINTRICARBOXYLIC ACID

AURINTRICARBOXYLIC ACID synthesis

6synthesis methods

Product Name:AURINTRICARBOXYLIC ACID
CAS Number:4431-00-9
Molecular formula:C22H14O9
Molecular Weight:422.34

50-00-0 Synthesis

50-00-0
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$10.00/25g

69-72-7 Synthesis

69-72-7
1273 suppliers
$5.00/10g

4431-00-9
122 suppliers
$37.70/5g

Yield:4431-00-9 91%

Reaction Conditions:

Stage #1:salicylic acid with sulfuric acid;sodium nitrite at 20;
Stage #2:formaldehyd at 0 - 5;

Steps:

Synthesis of aurintricarboxylic acid (ATA)
A short-necked flask containing 10 mL of concentrated sulfuric acid was immersed in an ice-water bath with strong stirring, and 1.428 g of solid sodium nitrite was added in small parts. The addition is accompanied by the emission of nitrogen oxides. When solution is complete, 2.857 g of salicylic acid is added in small parts with stirring for about 10 min. The mixture is stirred at 20 °C until all the solid dissolves in the solution. The mixture should then be colored light red to brown, very viscous and homogeneous. When the temperature reaches 0 °C, 0.7 mL of 35-40% solution of formaldehyde is slowly added with strong stirring. The temperature should not exceed 5 °C. The reaction is complete after all the formaldehyde has been added. Finely about 5 g of crushed ice is added, followed by 70 mL of ice water. The stirring should be strong during the addition. The flask content is stirred until the aurintricarboxylic acid breaks down into small parts. The solid was washed with cold water several times and filtered with suction. It is then dried at 40-50 °C. The yield is 2.055 g (91%); pale red crystals; m.p. : (246-250 °C); 1H NMR (500 MHz, DMSO-d6) δ ppm: 11.57 (brs, 3H, 3 OH, carboxylic acid groups), 8.17 (s, 1H, Ar-H), 7.78 (d, J = 8.7 Hz, 1H, Ar-H), 7.79-7.09 (m, 6H, Ar-H), 6.93-6.82 (m, 1H, Ar-H), 5.59 (brs, 2H, 2 OH, phenol groups); MS (ESI): m/z = 423 [M+ + H].

References:

Hilal;Hanoon [Research on Chemical Intermediates,2020,vol. 46,# 2,p. 1521 - 1538]

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