Methanol → Methyl 3-iodobenzoate

HRID 2278463Notes

Reaction equation

HRID 2278463 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].OS(O)(=O)=O.O.[CH3:17]O>>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH3:17])=[O:6]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 1118Sulfuric AcidHCID 120603-Iodobenzoic acid

Product 1

HCID 69258Methyl 3-iodobenzoate

Procedure

To a solution of 3-iodobenzoic acid (50.0 g, 0.202 mol) in methanol (300.0 ml) was added H2SO4 (1.0 ml). The reaction mixture was heated to reflux. After reflux 24 h, heating was stopped. The reaction mixture was cooled to room temperature. Water (400.0 ml) was added, the product was extracted with ethyl acetate (2×300.0 ml). The organic layer was washed with 20% of NaHCO3 water solution and followed with water. After removal of ethyl acetate, the crude product was purified by recrystallization from ethanol/water. Final white pure product was obtained in 51.0 g (96.5%) after dry under vacuum. 1H NMR (400 MHz, CDCl3, δ): 8.35 (t, J=1.6 Hz, 1H), 7.97 (dt, J1=8.4 Hz, J2=1.6 Hz, 1H), 7.85 (dt, J1=8.4 Hz, J2=1.6 Hz, 1H), 7.14 (t, J=8.4 Hz, 1H), 3.89 (s, 3H, OCH3). 13C NMR (100 MHz, CDCl3, δ): 165.56, 141.70, 138.42, 131.93, 130.03, 128.70, 93.76, 52.38.

Workup

  1. temperatureThe reaction mixture was heated to reflux
  2. temperatureAfter reflux 24 h
  3. temperatureheating
  4. extractionthe product was extracted with ethyl acetate (2×300.0 ml)
  5. washThe organic layer was washed with 20% of NaHCO3 water solution
  6. customAfter removal of ethyl acetate
  7. customthe crude product was purified by recrystallization from ethanol/water
  8. customFinal white pure product was obtained in 51.0 g (96.5%)
  9. customafter dry under vacuum

Sources & evidence

ORD record
ord-9400d69ba7fa415ca9a458752714cb55
Source dataset
uspto-grants-2015_09
Patent number
US09133177B2

Reaction notes

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