Hydrochloric Acid → Ethyl 2-iodo-3-methylbenzoate

HRID 1047900Notes

Reaction equation

HRID 1047900 reaction equation
[I:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl.[CH3:13][CH2:14]O>>[CH2:13]([O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[C:10]([CH3:11])[C:2]=1[I:1])[CH3:14]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 27593652-Iodo-3-methylbenzoic acid

Product 1

HCID 12140519Ethyl 2-iodo-3-methylbenzoate

Conditions

Temperature
0 °C

Procedure

A solution of the 2-iodo-3-methylbenzoic acid (6 g-0.023 mol) in EtOH (150 mL) is treated with concentrated HCl (20 mL) and refluxed for 48 h. After removal of the EtOH in vacuo, the residue is diluted with water (125 mL) and cooled to 0° C. in an ice bath. The pH is adjusted to 10 with solid NaOH pellets and extracted with EtOAc (3×75 mL). The organic extracts are washed with water (2×50 mL) and brine (2×50 mL) and dried over MgSO4. Concentrated in vacuo to give the product as a pale yellow oil. (6 g, 90%).

Workup

  1. temperaturerefluxed for 48 h
  2. customAfter removal of the EtOH in vacuo
  3. additionthe residue is diluted with water (125 mL)
  4. extractionextracted with EtOAc (3×75 mL)
  5. washThe organic extracts are washed with water (2×50 mL) and brine (2×50 mL)
  6. dry with materialdried over MgSO4
  7. concentrationConcentrated in vacuo

Sources & evidence

ORD record
ord-3d7235a953834012b251cecc2b60ac2f
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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