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Methyl 4-isopropyl-3,5-dimethoxybenzoate

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Methyl 4-isopropyl-3,5-dimethoxybenzoate Basic information

Product Name:
Methyl 4-isopropyl-3,5-dimethoxybenzoate
Synonyms:
  • BENV-003
  • Benvitimod Intermediates
  • methyl 4-isopropyl-3,5-dimethoxybenzoate
  • Benzoic acid, 3,5-dimethoxy-4-(1-methylethyl)-, methyl ester
  • Methyl 3,5-dimethoxy-4-isopropylbenzoate
CAS:
344396-17-4
MF:
C13H18O4
MW:
238.28
Mol File:
344396-17-4.mol
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Methyl 4-isopropyl-3,5-dimethoxybenzoate Chemical Properties

Boiling point:
338.3±42.0 °C(Predicted)
Density 
1.057±0.06 g/cm3(Predicted)
InChI
InChI=1S/C13H18O4/c1-8(2)12-10(15-3)6-9(13(14)17-5)7-11(12)16-4/h6-8H,1-5H3
InChIKey
TVZJWLXRNLZUBP-UHFFFAOYSA-N
SMILES
C(OC)(=O)C1=CC(OC)=C(C(C)C)C(OC)=C1
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Methyl 4-isopropyl-3,5-dimethoxybenzoate Usage And Synthesis

Synthesis

Anhydrous AlCl3 (0.85 g) was added to dry CS2 (100 mL) containing methyl 3,5-dimethoxy-benzoate (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), and 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 4-isopropyl-3,5-dimethoxybenzoate (0.69 g, 66%), which was crystallized from EtOH/Hexanes.

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