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CAS No. : | 1087-26-9 | MDL No. : | MFCD00051936 |
Formula : | C13H18O5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DQHJNOHLEKVUHU-UHFFFAOYSA-N |
M.W : | 254.28 | Pubchem ID : | 9831030 |
Synonyms : |
Hexyl 3,4,5-trihydroxybenzoate
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P264-P270-P272-P280-P301+P312-P302+P352-P330-P333+P313-P363-P403-P501 | UN#: | N/A |
Hazard Statements: | H302-H317 | Packing Group: | N/A |
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 |
---|---|---|
98% | With sulfuric acid at 100℃; for 0.833333h; Microwave irradiation; | 4.1.1. Microwave assisted conditions for the synthesis of alkyl gallates 2-7 General procedure: A microwave vial was loaded with gallic acid 1 (0.3mmol, 50mg), the corresponding alcohol (0.9mmol), and concentrated H2SO4 (0.07mL). The reaction vessel was sealed and irradiated in a microwave reactor at 100°C for 50min. After cooling, volatiles were evaporated to dryness and the residue was dissolved in ethyl acetate (30mL) and washed successively with saturated solutions of NaHCO3 (3×20mL) and NaCl (1×20mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under vacuum. The residue was then purified by column chromatography using hexane/EtOAc, (3:7) as the eluent. Melting points and characterization of compounds 2-7 were consistent with those found in the literature [25d]. In our case, the following yields were obtained: 2 (70%), 3 (97%), 4 (83%), 5 (98%), 6 (96%), 7 (82%). |
92% | With brominated hydrophobically modified sulfonic acid resin at 150℃; for 10h; | 12 100 g of gallic acid and 450 g of n-hexanol were weighed into a reactor,And 50 g of Reference Example 2 was added theretoThe resulting brominated hydrophobically modified sulfonic acid resin,Heating and heating to 150 DEG C for 10 hours, filtering, obtaining filtrate and recovering brominated modified sulfonic acid resin; the filtrate obtained in step (1) is distilled off excess alcohol to obtain the crude product, and then recrystallization, dewatering and drying by deionized water to obtain n-hexyl gallate, the yield is 92%, the product purity is 99.8% . |
72% | Stage #1: 3,4,5-trihydroxybenzoic acid; hexan-1-ol With diisopropyl-carbodiimide In tetrahydrofuran at 0℃; for 0.5h; Stage #2: With dmap In tetrahydrofuran at 20℃; for 24h; | Esterification reaction General procedure: A solution of gallic acid or 3,4,5-trimethoxygallic acid (1 mmol), alcohols (2 mmol)and 1.5 mmol diisopropyl carbadiimide (DIC) as catalisator in tetrahydofurane (10 mL) were stirred in 0 °C for 30 min. then added solution of 0,1 mmol N,N-Dimethylaminopiridine (DMAP) in 1 ml THF. This mixture was stirred at room temperature for 24 hours. The reaction mixture was then added aquadest and extracted with chloroform. The organic phase was then added Mg2SO4 anhydrate to take out the water residue. The filtrate was then drying to obtain the crude product. The product was purified using chromatography colomn with appropriate mobile phase. |
67% | With sulfuric acid In toluene Heating; | |
58% | With dicyclohexyl-carbodiimide In tetrahydrofuran for 20h; | |
58% | With dicyclohexyl-carbodiimide In tetrahydrofuran for 20h; | |
56% | With dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃; for 20h; | |
52% | Stage #1: 3,4,5-trihydroxybenzoic acid; hexan-1-ol With diisopropyl-carbodiimide In tetrahydrofuran at 0℃; for 1h; Stage #2: With dmap In tetrahydrofuran at 0℃; for 6h; | General procedure of esterification of gallic acid General procedure: To the solution containing gallic acid (250 mg, 1.47 mmol) in THF solvent at 0° C is added alcohol (2.94 mmol) and the DIC (0.34 mL, 2.205 mmol) as an activator. The reaction mixture was stirred for 1 h at 0° C, then added DMAP catalyst(18 mg, 0.147 mmol), and stirred again for the next 6 h at 0° C, then allowed to reach room temperature.The reaction was terminated when the TLC analysis showed no spot of the remaining gallic acid. After the reaction is complete, the reaction mixture is diluted with ether, filtered, evaporated,and purified by column silica gel chromatography. Pure compounds were analyzed by Thin Layer Chromatography (TLC), Nuclear Magnetic Resonance Spectrometer (NMR), and High Resolution Mass Spectrometer (HRMS) |
43% | With sulfuric acid Reflux; | |
With hydrogenchloride | ||
With sulfuric acid at 110℃; for 5h; | ||
With dicyclohexyl-carbodiimide In 1,4-dioxane at 5℃; for 48h; | ||
With dicyclohexyl-carbodiimide In tetrahydrofuran; dichloromethane at 20℃; | ||
With sulfuric acid In toluene Reflux; Dean-Stark; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With dihydrogen peroxide; horseradish peroxidase In aq. phosphate buffer; acetone |