Methanol → Benzoic acid, 2-iodo-5-methyl-, methyl ester

HRID 1477738Notes

Reaction equation

HRID 1477738 reaction equation
OS(O)(=O)=O.[I:6][C:7]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].[OH-].[Na+].[CH3:19]O>>[I:6][C:7]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:8]=1[C:9]([O:11][CH3:19])=[O:10]

Participants

5

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 1429412-Iodo-5-methylbenzoic acid

Product 1

HCID 14263946Benzoic acid, 2-iodo-5-methyl-, methyl ester

Procedure

H2SO4 95-98% (2.54 mL, 0.048 mol) was added to a solution of 2-iodo-5-methylbenzoic acid (25.0 g, 0.095 mol) in MeOH (220 mL) and refluxed for 20 h. The rxn mixture was cooled with an ice bath, and 1N aq. NaOH was added dropwise until pH 8 was reached. The org. solvent was removed in vacuo and the aq. layer was extracted with DCM (2×). The combined org. extracts were washed with sat. aq. NaHCO3 (1×) and H2O (1×), dried (Na2SO4), filtered and concentrated in vacuo to give methyl 2-iodo-5-methylbenzoate as a pale yellow liquid which was used in the next step without further purification. LC-MS A: tR=0.87 min; [M+H]+=259.22.

Workup

  1. temperaturerefluxed for 20 h
  2. temperatureThe rxn mixture was cooled with an ice bath
  3. customsolvent was removed in vacuo
  4. extractionthe aq. layer was extracted with DCM (2×)
  5. washextracts were washed with sat. aq. NaHCO3 (1×) and H2O (1×)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-35b0647c6c134a23a0dbe03c2ff28480
Source dataset
uspto-grants-2016_08
Patent number
US09403813B2

Reaction notes

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