A class of water-soluble sodium carboxyl-containing hydroxybenzocoumarin sulfonate and its preparation method and application
A technology of sodium coumarin sulfonate and benzocoumarin carboxylic acid, which is applied in chemical instruments and methods, fluorescence/phosphorescence, instruments, etc., and can solve application limitations, poor fat solubility and water solubility, and difficulty in penetrating biomembranes etc. to achieve the effects of high utilization rate of raw materials, easy operation and low production cost
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Embodiment 1
[0037] Preparation of compounds a~d
[0038] Add 0.5 g of 7-hydroxy-6-oxo-6H-benzo[c]chromene-8-carboxylic acid into a 25 mL reactor, and slowly add 2.0 mL of sulfuric acid with a mass concentration of 98%, dropwise After completion, react at 60°C for 2 hours. After the reaction is complete, cool it down, pour it into saturated NaCl aqueous solution, and precipitate a light yellow precipitate. After filtering the precipitate, salting out and purifying, the pure product of compound a is obtained.
[0039] In this example, the same mass of 7-hydroxy-3-methoxy-6-oxo-6H-benzo[c]chromene-8-carboxylic acid, 3,7-dihydroxy-6- Oxo-6H-benzo[c]chromene-8-carboxylic acid, 1,7-dihydroxy-6-oxo-6H-benzo[c]chromene-8-carboxylic acid were replaced by For 7-hydroxy-6-oxo-6H-benzo[c]chromene-8-carboxylic acid in Example 1, other steps were the same as in Example 1 to obtain compounds b, c, and d sequentially.
[0040] Table 1 Substituents, chemical names and yields of compounds a~d
[0041] ...
Embodiment 2
[0054] In this example, the amount of sulfuric acid with a mass concentration of 98% was 3.0 mL. Other steps were the same as in Example 1 to obtain compounds a to d. The yields of each compound are shown in Table 3.
[0055] The productive rate of compound a~d when table 3 solid-liquid ratio is 1g:6mL
[0056] compound a compound b compound c compound d 70％ 58％ 43％ 51％
Embodiment 3
[0058] In this example, the amount of sulfuric acid with a mass concentration of 98% was 1.5 mL. Other steps were the same as in Example 1 to obtain compounds a to d. The yields of each compound are shown in Table 4.
[0059] The productive rate of compound a~d when table 4 solid-liquid ratio is 1g:3mL
[0060] compound a compound b compound c compound d 66％ 53％ 33％ 48％
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