Iodoacetic Acid → HCID 13958742, compound

HRID 255943

Reaction equation

HRID 255943 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9](=[O:12])[CH:10]=[CH2:11])[CH:5]=[CH:4][C:3]=1[OH:13].I[CH2:15][C:16]([OH:18])=[O:17].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9](=[O:12])[CH:10]=[CH2:11])[CH:5]=[CH:4][C:3]=1[O:13][CH2:15][C:16]([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 5240Iodoacetic AcidHCID 11430Potassium CarbonateHCID 13958744HCID 13958744, compound

Product 1

HCID 13958742HCID 13958742, compoundYield 35.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2,3-Dichloro-4-acryloylphenol (4.85 g, 0.0224 mole), iodoacetic acid (4.5 g, 0.24 mole), potassium carbonate (3.33 g, 0.024 mole) and acetone (200 ml) were united, stirred and refluxed for 20 hours. The reaction mixture was cooled and the solid removed by filtration, dissolved in water (100 ml) and acidified to a pH of 1 with concentrated hydrochloric acid. The material that separated was extracted with chloroform, the organic layer removed, washed with water, dried over MgSO4, filtered and the solvent removed by evaporation in vacuo. The residue was recrystallized from carbon tetrachloride to give 2.2 g of (2,3-dichloro-4-acryloylphenoxy)-acetic acid, m.p. 111°-113° C.

Workup

  1. temperaturerefluxed for 20 hours
  2. temperatureThe reaction mixture was cooled
  3. customthe solid removed by filtration
  4. dissolutiondissolved in water (100 ml)
  5. customThe material that separated
  6. extractionwas extracted with chloroform
  7. customthe organic layer removed
  8. washwashed with water
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. customthe solvent removed by evaporation in vacuo
  12. customThe residue was recrystallized from carbon tetrachloride

Sources & evidence

ORD record
ord-e78cce5e0b18492bb04bdc49b63ef128
Source dataset
uspto-grants-1987_10
Patent number
US04699926

Linked notes

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