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Chemical Structure| 1466-76-8 Chemical Structure| 1466-76-8
Chemical Structure| 1466-76-8

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2,6-Dimethoxybenzoic acid is a natural product isolated and purified from the herbs of Curculigo orchioides. showing antimicrobial activity against several bacteria (S. aureus, E. coli, P. aeruginosa, and B. subtilis) and fungi (C. albicans and T. mentagrophytes).

Synonyms: 2,6-Dimethoxybenzoic acid

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Product Details of 2,6-Dimethoxybenzoic acid

CAS No. :1466-76-8
Formula : C9H10O4
M.W : 182.17
SMILES Code : O=C(O)C1=C(OC)C=CC=C1OC
Synonyms :
2,6-Dimethoxybenzoic acid
MDL No. :MFCD00002437
InChI Key :MBIZFBDREVRUHY-UHFFFAOYSA-N
Pubchem ID :15109

Safety of 2,6-Dimethoxybenzoic acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 2,6-Dimethoxybenzoic acid

* 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.

  • Downstream synthetic route of [ 1466-76-8 ]

[ 1466-76-8 ] Synthesis Path-Downstream   1~11

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  • concentrated aq. barium hydroxide solution [ No CAS ]
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  • [ 2734-70-5 ]
YieldReaction ConditionsOperation in experiment
With 4-methyl-morpholine; diphenylphosphoranyl azide; hydrogen; copper(I) iodide; benzyl alcohol;palladium; In methanol; 1,2-dichloro-ethane; Example 16A 2,6-Dimethoxyaniline To a stirred solution of 2,6-dimethoxybenzoic acid (2.00 g, 11.0 mmol) in 1,2-dichloroethane (45 mL) at ambient temperature was successively added N-methylmorpholine (1.45 mL, 13.2 mmol) and diphenylphosphoryl azide (2,60 mL, 12.1 mmol). After heating the mixture for 2 hours at 75 C., cuprous iodide (150 mg) and benzyl alcohol (2.27 mL, 22.0 mmol) were added and heating was continued overnight. Solvents were removed in vacuo and the residue was chromatographed on silica gel, eluding with 4:1 hexane-ethyl acetate to give the intermediate carbamate (1.50 g, 48 % yield) as a white, crystalline solid. The solid was dissolved in methanol (15 mL) and added to a flask purged with nitrogen containing 10% palladium-on-charcoal (500 mg). The mixture was placed under a balloon of hydrogen and stirred 4 hours at ambient temperature. The mixture was filtered through a pad of Celite and solvents were removed in vacuo to give the title compound (800 mg, 48% yield).
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  • [ 931-97-5 ]
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  • 7
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  • [ 16932-45-9 ]
YieldReaction ConditionsOperation in experiment
84% With silver carbonate; copper(ll) bromide; palladium dichloride; In tetrahydrofuran; at 110℃; for 24h; General procedure: A mixture of carboxylic acid (1 equiv., 0.5 mmol), CuBr2 or CuCl2 (2 equiv., 1 mmol), Ag2CO3 (1 equiv., 0.5 mmol) and PdCl2 (0.1 equiv.) was heated inTHF (3 mL) under reflux at 110 oC for 24 h. After the reaction finished, the mixture was evaporated under vacuum and purified by columnchromatography to afford the desired product.
  • 8
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  • [ 7051-15-2 ]
YieldReaction ConditionsOperation in experiment
25% With silver carbonate; copper dichloride; palladium dichloride; In tetrahydrofuran; at 110.0℃; for 24.0h; General procedure: A mixture of carboxylic acid (1 equiv., 0.5 mmol), CuBr2 or CuCl2 (2 equiv., 1 mmol), Ag2CO3 (1 equiv., 0.5 mmol) and PdCl2 (0.1 equiv.) was heated inTHF (3 mL) under reflux at 110 oC for 24 h. After the reaction finished, the mixture was evaporated under vacuum and purified by columnchromatography to afford the desired product.
  • 9
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  • [ 22795-99-9 ]
  • [ 96947-76-1 ]
YieldReaction ConditionsOperation in experiment
84.5% Synthesis of Compound (1) (S)-(-)-N-[(1-Ethyl-2-pyrrolidinyl)methyl]-2,6-dimethoxybenzamide Take 2.8 g (15.4 mmol) 2,6-dimethoxybenzoic acid and add with 20 mL hexane and 2.4 mL (33.3 mmol) thionyl chloride. Heat and reflux for 2 hours and evaporate all volatile substances under reduced pressure. Then dissolve the residue in methylene chloride (20 mL) and slowly drop 20 mL methylene chloride containing 2.0 g (15.6 mmol) (S)-(-)-2-aminomethyl-1-ethylpyrrolidine into the methylene chloride solution. Stir the solution at room temperature overnight. Next wash the reaction solution with saturated sodium bicarbonate aqueous solution (40 mL) and the reaction solution separates into two phases. The organic phase is dried by anhydrous sodium sulfate (Na2SO4) and then is concentrated under reduced pressure. The residue is separated and purified by liquid chromatography (silicon dioxide(SiO2), dichloromethane(CH2Cl2): methanol(CH3OH)=100:15) to get colorless solid product, the compound (1) (3.8 g, 84.5%). [0034] Compound data of the product: [0035] IR (KBr) nu 3324 (NH), 1663 (CO) cm-1. [0036] 1H NMR (CDCl3) delta 7.15 (t, J=8.4 Hz, 1H, Ph), 6.45 (d, J=8.4 Hz, 2H, Ph), 6.32 (br, 1H, NH), 3.69 (m, 7H, OCH3 and NHCH2), 3.16 (m, 1H, NHCH2), 3.03 (m, 1H, CH2CH2CH2N), 2.77 (m, 1H, CH2CH3), 2.57 (m, 1H, CH), 2.11 (m, 2H, CH2CH3 and CH2CH2CH2N), 1.84-1.58 (m, 3H, CH2CH2CH2N), 0.99 (t, J=7.4 Hz, 3H, CH2CH3). 13C NMR (CDCl3) delta 165.19 (CO), 156.26, 129.36, 115.29 and 102.92 (Ph), 61.72 (CH), 54.79 (OCH3), 52.47 (CH2), 47.05 (CH2), 39.53 (CH2), 26.70 (CH2), 21.70 (CH2), 21.70 (CH2), 12.60 (CH3). MS m/z 292 (M+), 264 (M+-CH2CH3+1), 195 (M+-CH3CH2N(CH2)3CH+1), 165 (M+-CH3CH2N(CH2)3CHCH2N), 98 ((CH3CH2N-(CH2)3CH)+).
80% General procedure: Benzoic acid derivatives (1 mmol) and heterogeneous catalyst (10 mg) were mixed for 5 min in 1 mL of anhydrous toluene. Then, the amine (1.2 mmol) was added and the mixture was reacted under ultrasound for about 15-60 min at room temperature. After completion of the reaction (monitored by TLC), the catalyst was separated through filtration and the solvent was removed in vacuo. The obtained residue was dissolved in chloroform (10 ml) and washed with 10% NaHCO3 (10 ml) and HCl (1 M, 10 ml). The organic layer was extracted and dried over Na2SO4 and concentrated under reduced pressure to afford the amide, which was purified by recrystallization or column chromatography.
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  • potassium ferrocyanide [ No CAS ]
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  • [ 55305-43-6 ]
  • [ 16932-49-3 ]
 

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