Sulfuric Acid → HCID 22285020, compound

HRID 984847Notes

Reaction equation

HRID 984847 reaction equation
[I:1][C:2]1[C:3]([C:12]([OH:14])=[O:13])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.OS(O)(=O)=O.[C:20]([O-])(O)=O.[Na+]>CO>[I:1][C:2]1[C:3]([C:12]([O:14][CH3:20])=[O:13])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 114607143-iodo-2-naphthoic acid

Product 1

HCID 22285020HCID 22285020, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 3-iodo-2-napthoic acid (Preparation 5) (6.50 g), were added MeOH (100 mL) and concentrated H2SO4 (2 mL), and the resultant heterogeneous mixture was refluxed for 13 hr. The reaction mixture was allowed to cool to RT, then neutralized with NaHCO3 (6.0 g), and the volatile component was removed in vacuo. The residue was partitioned between water (50 mL) and EtOAc (300 mL). The organic layer was washed with Na2S2O3 solution (4.2 g +50 mL of water) and brine, dried (MgSO4), filtered and evaporated in vacuo. The resulting crude material was submitted to flash chromatography (sample was loaded as a silica gel mesh, 10% EtOAc/hexanes) to isolate the title compound as a light-yellow solid (5.50 g, 2 steps combined yield of 69%). 1H NMR (DMSO, δ=2.50): 8.66 (s, 1H), 8.39 (s, 1H), 8.06 (d, J=8.0, 1H), 7.95 (d, J=8.0, 1H), 7.69-7.62 (m, 2H), 3.91 (s, 3H). (DCI) m/z (M+H)+=313.0. Anal. calculated for C12H9IO2: C, 46.18; H, 2.91. Found: C, 46.28; H, 2.85.

Workup

  1. temperaturethe resultant heterogeneous mixture was refluxed for 13 hr
  2. customthe volatile component was removed in vacuo
  3. customThe residue was partitioned between water (50 mL) and EtOAc (300 mL)
  4. washThe organic layer was washed with Na2S2O3 solution (4.2 g +50 mL of water) and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-60e04932cd0e4c3cbcd8b114501e893d
Source dataset
uspto-grants-2005_03
Patent number
US06869956B2

Reaction notes

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