Iodoacetic Acid → (2,3-Dichloro-4-acryloylphenoxy)-acetic acid

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

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.