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[ CAS No. 344396-17-4 ] {[proInfo.proName]}

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Chemical Structure| 344396-17-4
Chemical Structure| 344396-17-4
Structure of 344396-17-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 344396-17-4 ]

CAS No. :344396-17-4 MDL No. :
Formula : C13H18O4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 238.28 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 344396-17-4 ]

* 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 [ 344396-17-4 ]

[ 344396-17-4 ] Synthesis Path-Downstream   1~5

  • 2
  • [ 2150-37-0 ]
  • [ 344396-17-4 ]
YieldReaction ConditionsOperation in experiment
In CS2; isopropyl bromide 1.ii (a) (ii) Methyl 3,5-dimethoxy-4-isopropyl-benzoate (compound 3 in Scheme 1): anhydrous AlCl3 (0.85 g) was added to dry CS2 (100 mL) containing methyl 3,5-dimethoxy-benzoate (compound 2 in Scheme 1) (0.86 g) and 2-bromopropane (0.61 mL, 1.1 eq.). This solution was heated to reflux for 7 days. The mixture was filtered, washed with water (100 mL*2), saturated NaHCO3 (100 mL) and saturated NaCl (100 mL), dried over Na2SO4. After filtration and removal of the solvent, the crude product was purified by column chromatographyy (EtOAc/Hexanes=4:1) to give methyl 3,5-dimethoxy-4-isopropyl-benzoate (compound 3) (0.69 g, 66%) which was crystallized from EtOH/Hexanes. NMR (100 MHz, CDCl3) δ1.61 (d, 6 H, J1',2'=7.1 Hz, H-2'), 3.66 (hept, 1 H, H-1'), 3.88 (s, 6 H, OCH3), 3.94 (s, 3 H, COOCH3), 7.25 (s, 2 H, H-2,6).
In CS2; isopropyl bromide 1.ii (a) (ii) Methyl 3,5-dimethoxy-4-isopropyl-benzoate (compound 3A in Scheme 4): anhydrous AlCl3 (0.85 g) was added to dry CS2 (100 mL) containing methyl 3,5-dimethoxy-benzoate (compound 2A in Scheme 4) (0.86 g) and 2-bromopropane (0.61 mL, 1.1 eq.). This solution was heated to reflux for 7 days. The mixture was filtered, washed with water (100 mL*2), saturated NaHCO3 (100 mL) and saturated NaCl (100 mL), dried over Na2SO4. After filtration and removal of the solvent, the crude product was purified by column chromatography (EtOAc/Hexanes=4:1) to give methyl 3,5-dimethoxy-4-isopropyl-benzoate (compound 3A) (0.69 g, 66%) that was crystallized from EtOH/Hexanes. NMR (100 MHz, CDCl3): δ 1.61 (d, 6H, J1',2'=7.1 Hz, H-2'), 3.66 (hept, 1H, H-1'), 3.88 (s, 6H, OCH3), 3.94 (s, 3H, COOCH3), 7.25 (s, 2H, H-2,6).
  • 4
  • [ 75-29-6 ]
  • [ 2150-37-0 ]
  • [ 344396-17-4 ]
YieldReaction ConditionsOperation in experiment
81% With aluminum (III) chloride; triethylamine hydrochloride at 0 - 20℃; for 8h; Large scale; 1 Example 1 Preparation of 4-isopropyl-3,5 dimethoxy-benzoic acid methyl ester Add 15kg of methyl 3,5-dimethylbenzoate into the 100L reactor,Triethylamine hydrochloride aluminum trichloride ionic liquid 30kg,At low temperature 0, add 30L of 2-chloropropane, after adding, stir at room temperature for 8h,The temperature was lowered to 0°C, the reaction solution was added 50L of methyl tert-butyl ether, separated, washed with water and spin-dried to obtain a white solid, which was recrystallized with methanol to obtain a white solid product of 14.75kg with a yield of 81%.
  • 5
  • [ 2150-37-0 ]
  • [ 75-26-3 ]
  • [ 344396-17-4 ]
YieldReaction ConditionsOperation in experiment
60% With aluminum (III) chloride In 1,2-dichloro-ethane at 90℃; for 6h; 1.1 (1) Preparation of methyl 3,5-dimethoxy-4-isopropylbenzoate (1) Weigh 3,5-dimethoxy-benzoic acid methyl ester (4g, 20.4mmol, 1eq) and 2-bromopropane (2.76g, 22.4mmol, 1.1eq) and dissolve in 1,2-dichloroethane (20mL ), under stirring, add anhydrous aluminum trichloride (2.98g, 22.4mmol, 1.1eq), heat to 90 degrees Celsius and stir for 6 hours. After the reaction is monitored by TLC, pour it into a 500mL beaker and add 200mL saturated carbonic acid. Sodium hydrogen solution was filtered, the filtrate was extracted with ethyl acetate, the organic solution was dried over magnesium sulfate, concentrated under reduced pressure, and separated by silica gel column to obtain product 1 (2.91g), a pale yellow solid, yield 60% .
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