Sulfamic Acid → 2-(4-Iodophenyl)propanoic acid

HRID 904237Notes

Reaction equation

HRID 904237 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:11])[CH:9]=[O:10])=[CH:4][CH:3]=1.S(=O)(=O)([OH:14])N.Cl([O-])=O.[Na+].S([O-])(O)=O.[Na+]>C(Cl)CCl.O>[I:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH3:11])[C:9]([OH:14])=[O:10])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 5987Sulfamic AcidHCID 233338292-(4-Iodophenyl)propanalHCID 23665763Sodium BisulfiteHCID 23668197Sodium Chlorite

Product 1

HCID 152255732-(4-Iodophenyl)propanoic acidYield 94.2%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent2×

Procedure

In 100 ml of ethylene chloride was dissolved 34 g of 2-(4-iodophenyl)propionaldehyde, and a solution of 16.5 g of sulfamic acid in 85 ml of water was added to the solution. A solution of 15.2 g of sodium chlorite in 22 ml of water was then dropped thereinto while keeping the solution at 10° to 15° C. The solution was stirred for 10 min, and 15 g of sodium hydrogen sulfite was added portionwise thereto. The organic layer was separated and then washed with water. To the organic layer was added 150 ml of 1 N aqueous sodium hydroxide solution, and the aqueous layer was then separated, after which the pH of the aqueous layer was adjusted to 3.0 with 6 N hydrochloric acid, upon which white crystals were precipitated. The crystals were collected by filtration, washed with water and then dried to obtain 34 g (yield 94%) of 2-(4-iodophenyl)propionic acid.

Workup

  1. customat 10° to 15° C
  2. customThe organic layer was separated
  3. washwashed with water
  4. additionTo the organic layer was added 150 ml of 1 N aqueous sodium hydroxide solution
  5. customthe aqueous layer was then separated
  6. customwere precipitated
  7. filtrationThe crystals were collected by filtration
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-e9ae42c9011d4b49ac19688d52552d69
Source dataset
uspto-grants-1980_10
Patent number
US04230719

Reaction notes

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