Methanol → Methyl 2-(2-iodophenyl)acetate

HRID 1711080Notes

Reaction equation

HRID 1711080 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].S(=O)(=O)(O)O.[CH3:17]O>>[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH3:17])=[O:10]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 27800902-Iodophenylacetic acid

Product 1

HCID 640185Methyl 2-(2-iodophenyl)acetateYield 95%

Procedure

A solution of 2-iodophenylacetic acid (5.05 g, 19.3 mmol) and sulfuric acid (0.5 mL) in methanol was heated under reflux for 6 h, then cooled and concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water, organic phase was collected, washed with 1M NaOH, brine, dried (MgSO4), filtered and concentrated to afford pure 318 (5.05 g, 95% yield). 1H NMR (400 MHz, CDCl3) δ (ppm): 7.85 (dd, J=8.0, 1.2 Hz, 1H); 7.34-7.27 (m, 2H); 6.97 (dt, J=7.6, 2.2 Hz, 1H); 3.81 (s, 2H); 3.73 (s, 3H).

Workup

  1. temperatureunder reflux for 6 h
  2. temperaturecooled
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was partitioned between ethyl acetate and water, organic phase
  5. customwas collected
  6. washwashed with 1M NaOH, brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-0d0933bc7f104345a55d3d6527c149d8
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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