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CAS No. : | 636-46-4 | MDL No. : | MFCD00010391 |
Formula : | C8H6O5 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | BCEQKAQCUWUNML-UHFFFAOYSA-N |
M.W : | 182.13 | Pubchem ID : | 12490 |
Synonyms : |
|
Chemical Name : | 4-Hydroxyisophthalic acid |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 | UN#: | |
Hazard Statements: | H315-H319 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With thionyl chloride; at 0 - 20℃; for 6.5h;Reflux; | Thionyl chloride (15 mL, 206 mmol) was added dropwise to a solution of 4-hydroxyisophthalic acid(5 g, 27.5 mmol, commercially available from, for example, Sigma Aldrich) in MeOH (50 mL) at 0 °Cunder nitrogen. The resulting solution was stirred at rt for 30 mm before heating gently to reflux for6 h. The reaction was allowed to cool. Upon cooling, a precipitate formed which was collected byfiltration to afford dimethyl 4-hydroxyisophthalate (5.32 g, 25.3 mmol, 92percent yield) as a white solid.LCMS (Formic): Retention time 1.02, poor ionisation1H NMR (DMSO-d6, 400 MHz): O (ppm) 11.01 (5, 1H), 8.36 (d, J=2.4 Hz, 1H), 8.04 (dd, J=8.6,2.4 Hz, 1H), 7.10 (d, J=8.6 Hz, 1H), 3.91 (5, 3H), 3.83 (5, 3H) |
86% | With thionyl chloride; for 3h;Reflux; | 20 g (109.9 mmol) of 4-hydroxyisophthalic acid was added to 330 mL of anhydrous methanol. With stirring at room temperature, 130 g (1099 mmol) of thionyl chloride was slowly added dropwise to the above solution and it was dripped within 40 minutes. After dripping, warm up to a slow reflux of the solution. The reaction was monitored by TLC (petroleum ether: ethyl acetate = 3:1) and the reaction was complete after 3 hours. After cooling to room temperature, a white solid precipitated. The solid was filtered and the cake was washed with plenty of water and dried in vacuo. The resulting solid was dissolved in 120 mL of ethyl acetate, and the ethyl acetate solution was washed with 90 mL of saturated sodium bicarbonate solution, 70 mL of distilled water, and 70 mL of saturated saline, dried over anhydrous sodium sulfate, filtered, and rotary evaporated to give 15 g of a white solid. The rate is 86%). |
With sulfuric acid; for 22h;Heating / reflux; | a) 4-Hydroxyisophthalic acid dimethyl ester To a solution of 4-hydroxyisophthalic acid (16.0 g) in methanol (150 mL) was added conc. sulfuric acid (5 mL), and the mixture was heated for 22 hours under reflux. Then, the reaction solution was allowed to stand for cooling down to room temperature, diluted with water (150 mL), and added with sodium bicarbonate (15 g). The resulting precipitate was filtered, washed successively with water/methanol (1:1, v/v) (150 mL) and water, and dried to give the title compound (17.45 g). |
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