Ethanol → HCID 67099316, compound

HRID 1868946Notes

Reaction equation

HRID 1868946 reaction equation
[Cl:1][C:2]1[C:3]([I:12])=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.OS(O)(=O)=O.[CH3:18][CH2:19]O>CCOC(C)=O>[Cl:1][C:2]1[C:3]([I:12])=[C:4]([CH2:8][C:9]([O:11][CH2:18][CH3:19])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 670999481035263-42-3

Product 1

HCID 67099316HCID 67099316, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(3-chloro-2-iodophenyl)acetic acid (3.2 g, 11 mmol) in 50 mL EtOH was treated with 2 mL con. H2SO4, and refluxed for 2 hours. The mixture was cooled to room temperature, diluted with 200 mL EtOAc, washed with water (3×50 mL), saturated NaCl (20 mL), dried over anhydrous sodium sulfate and concentrated. The concentrate was purified by column chromatography (10-20% EtOAc/hexane) to give 3.62 g pale yellow oil. MS m/e: (M+H)+ 325.

Workup

  1. additionwas treated with 2 mL con
  2. washwashed with water (3×50 mL), saturated NaCl (20 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe concentrate was purified by column chromatography (10-20% EtOAc/hexane)

Sources & evidence

ORD record
ord-c0347788d71244a4b6e43cdec0c784b7
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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