Benzenepropanoic acid → 3-(4-Iodophenyl)propanoic acid

HRID 2042971

Reaction equation

HRID 2042971 reaction equation
OS(O)(=O)=O.O.[C:7]1([CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[I:18]I>CC(O)=O.CCOC(C)=O>[I:18][C:10]1[CH:11]=[CH:12][C:7]([CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 107Benzenepropanoic acidHCID 807Iodine2×HCID 962WaterHCID 1118Sulfuric Acid

Product 1

HCID 2332383-(4-Iodophenyl)propanoic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of H2SO4 (1.25 mL), water (12.5 mL) and AcOH (25 mL) in a 250 mL flask and 3-phenylpropanoic acid (3.00 g, 20.0 mmol), iodine (1.40 g, 5.5 mmol) and KIO3 (0.98 g, 4.6 mmol) was added. The reaction was heated to reflux and a solution of iodine (1.40 g, 5.5 mmol) in AcOH (25 mL) was added in portions of 5 mL as the colour of the reaction faded from purple to orange. After 3 hours when no further colour changes appeared the reaction was cooled to room temperature. before quenching with 1M NaHSO3. The reaction was added water and extracted with EtOAc. The organic phases were combined, washed with brine, dried over MgSO4 and concentrated under vacuum. The product (4.15 g, 75%), containing minor impurites of starting material and the ortho-iodinated product, was recrystallised from PE to provide 1.83 g (33%) of the pure and white crystalline product. Rf: 0.10 (EtOAc:hexanes, 1:4); 1HNMR (CDCl3) δ 7.62-7.59 (m, 2H), 6.97-6.95 (m, 2H), 2.92-2.87 (t, 2H, J=7.5 Hz), 2.68-2.63 (t, 2H, J=7.5 Hz); 13CNMR (CDCl3) δ 178.5, 139.7, 137.6, 130.4, 91.6, 35.2, 30.0.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. custombefore quenching with 1M NaHSO3
  4. additionThe reaction was added water
  5. extractionextracted with EtOAc
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated under vacuum
  9. additionThe product (4.15 g, 75%), containing minor impurites of starting material
  10. customthe ortho-iodinated product, was recrystallised from PE
  11. customto provide 1.83 g (33%) of the pure and white crystalline product

Sources & evidence

ORD record
ord-7e0ab8d1f88649c787a49ab8ed3ec86e
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Linked notes

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