Hydrochloric Acid → 3-(2-iodophenyl)propanoic Acid

HRID 1432043Notes

Reaction equation

HRID 1432043 reaction equation
Cl.O.C([O:5][C:6](=[O:21])[CH:7]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[I:20])C(OCC)=O)C>CCOCC>[I:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][CH2:7][C:6]([OH:21])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 962Water2×HCID 141722941,3-Diethyl 2-[(2-iodophenyl)methyl]propanedioate

Product 1

HCID 27366673-(2-iodophenyl)propanoic Acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Concentrated HCl (2.3 mL) and water (0.3 mL) was added to 2-(2-iodo-benzyl)-malonic acid diethyl ester (1.4 g, 3.6 mmol) and the mixture was refluxed overnight. Starting material could still be seen on TLC. More concentrated HCl (2 mL) was added and the mixture was refluxed overnight. Water (20 mL) and ether (50 mL) was added to the mixture. The two phases was separated. The organic phase was extracted with an ammonium hydroxide solution (5N, 30 mL). The basic water phase was added slowly to ice-cold conc. HCl. The white precipitate was filtered and washed with ice-cold water and the solvent was removed in vacuo. Yield: 0.32 g, 32%.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. temperaturethe mixture was refluxed overnight
  3. customThe two phases was separated
  4. extractionThe organic phase was extracted with an ammonium hydroxide solution (5N, 30 mL)
  5. additionThe basic water phase was added slowly to ice-cold conc. HCl
  6. filtrationThe white precipitate was filtered
  7. washwashed with ice-cold water
  8. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d82795782b484ac89ddf73dc54dcc32c
Source dataset
uspto-grants-2009_11
Patent number
US07612068B2

Reaction notes

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