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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
3,4,5-Trimethoxyphenylacetic acid is a metabolite of mescaline, exhibiting antioxidant and anti-inflammatory properties.
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Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 951-82-6 |
Formula : | C11H14O5 |
M.W : | 226.23 |
SMILES Code : | C1=C(CC(O)=O)C=C(C(=C1OC)OC)OC |
MDL No. : | MFCD00004336 |
InChI Key : | DDSJXCGGOXKGSJ-UHFFFAOYSA-N |
Pubchem ID : | 70372 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315 |
Precautionary Statements: | P280 |
* 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 |
---|---|---|
68% | With lithium aluminium tetrahydride; In tetrahydrofuran; at 20℃;Cooling with ice; Inert atmosphere; Sealed tube; | To a 250 mL roundbottom flask was added a stir bar and freshly distilled THF (100 mL). The reaction vessel was cooled in an ice-water bath and stirring commenced. LAH (1.11 g, 30.0 mmol) was added in portions. The reaction vessel was sealed with a septa and flushed with nitrogen. In a separate vessel 3,4,5-trimethoxyphenylacetic acid (4.52 g, 20.0 mmol) was dissolved in THF (30 mL), and was added dropwise to the LAH/THF solution. The reaction was allowed to warm to room temperature and proceed overnight. The following day, the reaction vessel was cooled in an ice-water bath and the reaction was quenched with water (until gas no longer evolved) and concentrated HC1 (~ 1 mL). The reaction mixture was partitioned between ethyl acetate (200 mL) and water (100 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo to yield the crude product as a clear, yellow oil. The crude material was purified with silica gel chromatography (1 : 1 ethyl acetate: hexanes) to yield the final product as a yellow oil that solidified on standing (2.9 g, 68 %). Spectroscopic data matches that reported for this compound. NMR (500 MHz) (CDCL) d: 6.45 (2H, s), 3.87 - 3.83 (11H, m), 2.81 (2H, t, = 7.0, 7.0 Hz). 13C NMR (l25 MHz) (CDCL) d: 153.2, 136.5, 134.2, 105.8, 63.5, 60.8, 56.0, 39.5. M.P. = 40 C. |
With lithium aluminium tetrahydride;Inert atmosphere; | General procedure: The majority of alcohols were commercially available. Alcohols 9c,26 9i,27 9j28 and 9k29 were prepared by LiAlH4 reduction of the corresponding carboxylic acids and gave spectral data consistent with those in the literature. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | General procedure: The compound 3,4,5-trimethoxyphenyl acetic acid (8a) (200 mg, 0.88 mmol) was dissolved in 10 mL of Ac2O, followed by addition of substituted aldehyde 9a (136 mg, 0.88 mmol) and Et3N (1 mL). The reaction mixture was heated at 140 C for 12 h. After cooling, the reaction mixture was acidified with 35% aq HCl. The reaction mixture was left overnight and the precipitated product was filtered. The precipitate was recrystallized from absolute ethanol afford the pure compound 10a, 130 mg in 40% yield. | |
45% | With acetic anhydride; triethylamine; at 140℃; for 12h; | In a three-necked 100ml flask was added 3,4,5-trimethoxy phenyl acetic acid (2.4g, 10.6mmol), 3- nitro-4-methoxybenzaldehyde (1.92g, 10.6mmol), 2.4ml triethylamine amine and 24ml of acetic anhydride, heated with stirring to 140 , reaction 12h, heating was stopped, 14.4ml of concentrated hydrochloric acid was added dropwise, at room temperature overnight.There khaki solid precipitation, the reaction was stopped, filtered solids with about 150ml recrystallized from ethanol to give yellow needles of pure product 1.86g, yield 45.0% |
A mixture of 3,4,5-trimethoxyphenylacetic acid (8.84 mmol) and 3-nitro-4-methoxyenzaldehyde (4.4 mmol), acetic anhydride (4 mL) and triethylamine (2 mL) were heated under reflux for 3 h. After acidification with concentrated hydrochloric acid (6 mL), the resulting solid was filtered off and recrystallised from ethanol to give acrylic acid intermediate 11 as fine yellow needles. Subsequently the corresponding acrylic acid intermediate (5.56 mmol) was added to powdered copper (28.8 mmol) in quinoline (20 mL), and the resulting mixture was heated at 140 C for 2 h. Upon cooling, diethyl ether was added, and the copper was filtered off through Celite. The filtrate was washed with 1 M hydrochloric acid, and the aqueous layer was separated and extracted with diethyl ether. The combined organic layers were washed with saturated aqueous sodium carbonate, water, brine, dried (MgSO4), and concentrated in vacuo. Flash column chromatography (SiO2 petrol/EtOAc 7:3) and recrystallization from EtOAc and petrol afforded desired intermediate compound 12 in 52% yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63.1% | With acetic anhydride; triethylamine; at 140℃; for 18h; | In a three-necked 250ml flask was added 3,4,5-trimethoxy phenyl acetic acid (13.3g, 58.8mmol), 3- chloro-4-methoxybenzaldehyde (5g, 29.3mmol), 13.3ml triethylamine and 26.6ml of acetic anhydride, heated with stirring to 140 , 18H reaction, heating was stopped, concentrated hydrochloric acid was added dropwise 40ml, at room temperature overnight.There khaki solid precipitation, the reaction was stopped, filtered solids with about 100ml recrystallized from ethanol to give yellow needles 7.0g, yield 63.1percent |
Tags: 3,4,5-Trimethoxyphenylacetic acid | Carboxylic Acids | Aryls | Ethers | Organic Building Blocks | 951-82-6
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