Potassium Hydroxide → 12-(3-Iodophenyl)dodecanoic acid

HRID 2106982Notes

Reaction equation

HRID 2106982 reaction equation
C([O:3][C:4](=[O:23])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([I:22])[CH:17]=1)C.[OH-].[K+]>C(O)C>[I:22][C:18]1[CH:17]=[C:16]([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]([OH:23])=[O:3])[CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 14584162Ethyl-12-(m-iodophenyl)-dodecanoate

Product 1

HCID 1458416312-(3-Iodophenyl)dodecanoic acidYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl-12-(m-iodophenyl)-dodecanoate (7.17 g, 16.67 mmol), 95% ethanol (100 ml) and KOH (2.0 g) were placed into a 250 ml round-bottomed flask fitted with a reflux condenser. The reaction mixture was refluxed overnight. The ethanol was removed in vacuo and H2O was added. The aqueous solution was acidified and then extracted with ether. The ether layer was dried (MgSO4), and the solvent was evaporated to yield a yellow solid. The crude product was recrystallized with 95% ethanol to provide a white flaky solid, compound 7, 12-m-iodophenyldodecanoic acid (5.9 g, 88.0% yield).

Workup

  1. customfitted with a reflux condenser
  2. temperatureThe reaction mixture was refluxed overnight
  3. customThe ethanol was removed in vacuo and H2O
  4. additionwas added
  5. extractionextracted with ether
  6. dry with materialThe ether layer was dried (MgSO4)
  7. customthe solvent was evaporated
  8. customto yield a yellow solid
  9. customThe crude product was recrystallized with 95% ethanol

Sources & evidence

ORD record
ord-ced5cef72047470ebb1e917f35df89ae
Source dataset
uspto-grants-1990_06
Patent number
US04933157

Reaction notes

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