Ethyl Acetate → 3-(3,5-Dichlorophenyl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylic acid

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:13][C:12]([CH3:19])([C:14]([O:16]CC)=[O:15])[O:11][N:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[OH-].[Na+].C(OCC)(=O)C>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:13][C:12]([CH3:19])([C:14]([OH:16])=[O:15])[O:11][N:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

Procedure

5.00 g (16.55 mmol) of ethyl 3-(3,5-dichlorophenyl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate were dissolved in 50 ml of ethanol, and 24.82 ml of 1N NaOH were then added. After 1 h of stirring at RT, the solvent was removed, 100 ml of water were added and the aqueous phase was adjusted to pH 2 by addition of 2N HCl. The product formed was obtained by extraction with 100 ml of ethyl acetate, drying the organic phase over Na2SO4, filtration and concentration.