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

HRID 482185Notes

Reaction equation

HRID 482185 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-3c02e58b49a54cae82e9be0e6c25c9f5
Source dataset
uspto-grants-1998_08
Patent number
US05795561

Reaction notes

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