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

HRID 460493Notes

Reaction equation

HRID 460493 reaction equation
[C:1]([OH:11])(=[O:10])[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[I:12](O)(=O)(=O)=O.S(=O)(=O)(O)O.II>O.C(O)(=O)C>[I:12][C:7]1[CH:6]=[CH:5][C:4]([CH2:3][CH2:2][C:1]([OH:11])=[O:10])=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 107Benzenepropanoic acidHCID 807IodineHCID 1118Sulfuric AcidHCID 65185Metaperiodic acid

Product 1

HCID 2332383-(4-Iodophenyl)propanoic acidYield 460.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
105 °C

Procedure

Hydrocinnamic acid is iodinated to form 4-iodohydrocinnamic acid. The process is performed by mixing 201.2 g hydrocinnamic acid, 1 L acetic acid, 152 mL water, 52.8 g periodic acid, 76 mL sulfuric acid, and 144 g iodine. The mixture is heated at 105° C. for 6.5 hours. Next, 200 mL water is added, and the mixture is cooled to room temperature overnight. The solid product in the resultant mixture is filtered and washed with water, yielding 350 g unpurified 4-iodohydrocinnamic acid. Further purification is not necessary and is not conducted, and the product is used as is in the second step.

Workup

  1. temperaturethe mixture is cooled to room temperature overnight
  2. filtrationThe solid product in the resultant mixture is filtered
  3. washwashed with water

Sources & evidence

ORD record
ord-c4543b6f2743498eaf89c9a303be194c
Source dataset
uspto-grants-2007_03
Patent number
US07196214B2

Reaction notes

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