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

HRID 1274261Notes

Reaction equation

HRID 1274261 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 form 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 form methanol/water

Sources & evidence

ORD record
ord-0c1b33025f2e4dde9efd613106d3b064
Source dataset
uspto-grants-2000_12
Patent number
US06156784

Reaction notes

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