Sodium Hydroxide → 7-(2,4,6-Triiodophenoxy)heptanoic acid

HRID 2222721Notes

Reaction equation

HRID 2222721 reaction equation
[I:1][C:2]1[CH:19]=[C:18]([I:20])[CH:17]=[C:16]([I:21])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13]CC)=[O:12].[OH-].[Na+]>C(O)C>[I:1][C:2]1[CH:19]=[C:18]([I:20])[CH:17]=[C:16]([I:21])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22939821Ethyl 7-(2,4,6-triiodophenoxy)heptanoate

Product 1

HCID 229398227-(2,4,6-Triiodophenoxy)heptanoic acidYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethanol (95%, 30 mL) was added with of ethyl 7-(2,4,6-triiodophenoxy)-heptanoate (4.0 g) and the mixture was refluxed for dissolution, and the solution was added with sodium hydroxide (0.5 g) and further refluxed for 1.5 hours. The crystals obtained were separated by filtration, washed with ethanol and added with dichloromethane and 1 N hydrochloric acid to conduct extraction twice with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was removed. The resulting residue was purified by silica gel column chromatography to obtain 7-(2,4,6-triiodophenoxy)heptanoic acid (3.4 g, yield: 90%).

Workup

  1. temperaturethe mixture was refluxed for dissolution
  2. temperaturefurther refluxed for 1.5 hours
  3. customThe crystals obtained
  4. customwere separated by filtration
  5. washwashed with ethanol
  6. additionadded with dichloromethane and 1 N hydrochloric acid
  7. extractionextraction twice with dichloromethane
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  9. customthe solvent was removed
  10. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6f2af0f308884e1e90824cfa8181237b
Source dataset
uspto-grants-2008_05
Patent number
US07371877B2

Reaction notes

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