Iodine → 4-iodoBenzenepentanoic acid

HRID 2242772Notes

Reaction equation

HRID 2242772 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.II.C(O[I:20](C1C=CC=CC=1)OC(=O)C)(=O)C.C(OC(=O)C)(=O)C.S(=O)(=O)(O)O>C(O)(=O)C>[I:20][C:4]1[CH:5]=[CH:6][C:1]([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:2][CH:3]=1

Participants

7

Reactant 5

HCID 807IodineHCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 16757Benzenepentanoic acidHCID 76724Iodobenzene diacetate

Product 1

HCID 404797214-iodoBenzenepentanoic acidYield 129.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-Phenylpentanoic acid (50.0 g, 0.28 mol), iodine (37.77 g, 0.149 mol) and (diacetoxyiodo)benzene (48.0 g, 0.149 mol) are suspended in a mixture of glacial acetic acid (500 mL) and acetic anhydride (500 mL). Concentrated sulfuric acid (2 mL) is added and the suspension stirred for 2 h in the dark, during which the red colour fades. The solvent is removed under reduced pressure until approximately 80 ml remained, and the residue poured into ice-water (1 L) containing sodium metabisulfite (8 g). the resulting precipitate is stirred for 30 min, and then filtered. The crude product is recrystallised from ethanol/water, and then from acetic acid/water to afford the product (58.5 g). NMR showed the expected signals.

Workup

  1. customThe solvent is removed under reduced pressure until approximately 80 ml
  2. additionthe residue poured into ice-water (1 L)
  3. additioncontaining sodium metabisulfite (8 g)
  4. stirringthe resulting precipitate is stirred for 30 min
  5. filtrationfiltered
  6. customThe crude product is recrystallised from ethanol/water

Sources & evidence

ORD record
ord-9b0b6bbb31354c94898eb1dbb2288e1b
Source dataset
uspto-grants-2010_03
Patent number
US07674397B2

Reaction notes

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