18179-39-0

Hazard Information

Synthesis

16870-28-3

74-88-4

18179-39-0

General procedure for the synthesis of methyl 4-iodosalicylate from 2-hydroxy-4-iodobenzoic acid and iodomethane: 4-iodosalicylic acid (7.3 g, 27.65 mmol) was dissolved in 41 mL of DMF, NaHCO3 (2.78 g, 33.18 mmol) was added, and CO2 was released during the reaction and the mixture was stirred for 5 min. Iodomethane (2.66 mL, 5.85 g, 41.47 mmol, 1.5 eq.) was then added and the reaction mixture was heated with stirring at 40 °C for 5 h (the reaction progress was monitored by TLC). After completion of the reaction, the mixture was diluted with 170 mL of water and 170 mL of ethyl acetate (EA). The organic layer was washed sequentially with 170 mL of 5% NaHCO3 solution and 170 mL of 5% NaCl solution and dried with Na2SO4. Evaporation of the solvent gave about 9 g of crude product (in the form of a black oil), which was purified by column chromatography: 100 g of silica gel (SiO2) was used as stationary phase, and the eluent was pure hexane, which was subsequently adjusted to a solvent mixture of hexane:ethyl acetate (100:2). Finally, 5.86 g of pure product was obtained in 76.5% yield.

References

[1] Patent: US2016/2269, 2016, A1. Location in patent: Paragraph 0253; 0254

Questions And Answer

• Structure

  2-hy­droxy-4-iodo­benzoic acid methyl ester (methyl 4-iodo­salicylate, C8H7IO3) allows for an effective way of incorporating the methyl salicylates within larger organic mol­ecules, using such methodologies as McClure protocols, which take advantage of the iodine atom at the 4-position of the aromatic ring for the formation of carbon-carbon bonds. The iodine atom is also capable of forming supra­molecular synthons, which may be useful for crystal engineering. At 90 K, the methyl 4-iodo­salicylat displays monoclinic (P21/c) symmetry with one mol­ecule in the asymmetric unit. Inter­molecular hydrogen bonding inter­actions occur between the hy­droxy groups of one mol­ecule and the carbonyl oxygen atom of the methyl ester of an adjacent mol­ecule to form a centrosymmetric dimeric pair with H⋯O = 2.53 (4) Å. An O3—H3⋯O2 intra­molecular hydrogen bond also exists with an H⋯O distance of 2.05 (4) Å. The C5⋯C8 [3.326 (3) Å] and O3⋯H1C (2.51 Å) inter­actions provide only short contacts between the stacks of offset (102) parallel sheets, which make up the crystal. These sheets, in turn, contain the inversion-generated hydrogen-bonded dimers. The non-hydrogen atoms of the mol­ecule are essentially coplanar with no displacement from the mean mol­ecular plane greater than 0.132 Å.
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• Application

  4-Iodosalicylic acid methyl ester is an ester organic compound that can be used as a chemical reagent.;

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