Sulfuric Acid → 1-(4-Iodophenyl)cyclopropane-1-carboxylic acid

HRID 1387264Notes

Reaction equation

HRID 1387264 reaction equation
[C:1]1([C:7]2([C:10]([OH:12])=[O:11])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I:13]([O-])(=O)=O.[Na+].S(=O)(=O)(O)O>C(O)(=O)C>[I:13][C:4]1[CH:5]=[CH:6][C:1]([C:7]2([C:10]([OH:12])=[O:11])[CH2:9][CH2:8]2)=[CH:2][CH:3]=1

Participants

5

Reactant 3

HCID 1118Sulfuric Acid2×HCID 802061-Phenylcyclopropanecarboxylic acidHCID 23675764Sodium Iodate2×

Product 1

HCID 217064771-(4-Iodophenyl)cyclopropane-1-carboxylic acidYield 106%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1-phenylcyclopropane carboxylic acid (16.5 g, 101 mmol), sodium iodate (5.04 g) and concentrated sulfuric acid (1 mL) in acetic acid (70 mL) was stirred and heated at 70° C. for 2 days. Additional sodium iodate (1.88 g) and sulfuric acid (1 mL) were added, and stirring was continued for 1 day. The acetic acid was evaporated, and the residue was partitioned between ethyl acetate and water. The organic phase was washed with aqueous sodium thiosulfate, dried, filtered, and evaporated. The solid residue was recrystallized from methanol/water to give 1-(4-iodophenyl)cyclopropane-1-carboxylic acid (7.98 g, 27 mmol, 27%).

Workup

  1. stirringstirring
  2. customThe acetic acid was evaporated
  3. customthe residue was partitioned between ethyl acetate and water
  4. washThe organic phase was washed with aqueous sodium thiosulfate
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe solid residue was recrystallized from methanol/water

Sources & evidence

ORD record
ord-72580d1b8e6c4e5aaf335ac271d34fcb
Source dataset
uspto-grants-2001_07
Patent number
US06268365B1

Reaction notes

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