Ethanol → Ethyl 2-(2-chloro-6-iodophenyl)acetate

HRID 2078343Notes

Reaction equation

HRID 2078343 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([I:8])[C:3]=1[CH2:9][C:10]([OH:12])=[O:11].OS(O)(=O)=O.[CH3:18][CH2:19]O>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([I:8])[C:3]=1[CH2:9][C:10]([O:12][CH2:18][CH3:19])=[O:11]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 67099832(2-Chloro-6-iodophenyl)acetic acid

Product 1

HCID 67100056Ethyl 2-(2-chloro-6-iodophenyl)acetate

Procedure

A mixture of 2-(2-chloro-6-iodophenyl)acetic acid (10 g, 34 mmol) in 100 mL EtOH was treated with 2 mL concentrated H2SO4, and refluxed for 15 hours. The resulting mixture was cooled to room temperature and concentrated. The residue was diluted with 200 mL EtOAc, washed with water (3×50 mL), saturated NaCl (20 mL), dried over sodium sulfate and concentrated. The crude mixture was purified by column chromatography (10-20% EtOAc/hexane) to give 9.5 g of pale yellow oil. MS m/e: (M+H)+ 324.

Workup

  1. temperaturerefluxed for 15 hours
  2. concentrationconcentrated
  3. additionThe residue was diluted with 200 mL EtOAc
  4. washwashed with water (3×50 mL), saturated NaCl (20 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe crude mixture was purified by column chromatography (10-20% EtOAc/hexane)

Sources & evidence

ORD record
ord-ca4612a9e68745089749dd7e8f3a6273
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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