Methanol → Methyl 3-iodo-2-methylbenzoate

HRID 706161Notes

Reaction equation

HRID 706161 reaction equation
[I:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:17]O>>[CH3:17][O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([I:1])[C:3]=1[CH3:11]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 27348883-Iodo-2-methylbenzoic acid

Product 1

HCID 15656853Methyl 3-iodo-2-methylbenzoate

Procedure

A mixture of 3-iodo-2-methyl-benzoic acid (90 mmol, 23.6 g), methanol (250 mL), and concentrated sulfuric acid (13 mL) was refluxed with stirring for 40 h before it was concentrated in vacuo. The residue was dissolved in ethyl acetate and the mixture was neutralized by adding small portions of a saturated aqueous NaHCO3 solution with stirring. The organic phase was dried over MgSO4 and concentrated in vacuo to give the title compound as a yellowish oil (24.3 g); 1H NMR (CDCl3, 200 MHz): δ=7.96 (d, 1H), 7.71 (d, 1H), 6.91 (t, 1H), 3.89 (s, 3H), 2.66 (s, 3H).

Workup

  1. temperaturewas refluxed
  2. concentrationwas concentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. additionby adding small portions of a saturated aqueous NaHCO3 solution
  5. stirringwith stirring
  6. dry with materialThe organic phase was dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f3bab0d87aed45da8cd185f79f590999
Source dataset
uspto-grants-2015_11
Patent number
US09174976B2

Reaction notes

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