Sodium Hydroxide → 5-Benzoxazoleacetic acid, 2-(4-chlorophenyl)-
Reaction equation
Br[CH:2]([C:7]1[CH:8]=[CH:9][C:10]2[O:14][C:13]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)=[N:12][C:11]=2[CH:22]=1)[C:3]([O:5]C)=[O:4].[OH-].[Na+]>O1CCOCC1>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([C:13]2[O:14][C:10]3[CH:9]=[CH:8][C:7]([CH2:2][C:3]([OH:5])=[O:4])=[CH:22][C:11]=3[N:12]=2)=[CH:20][CH:19]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of methyl α-bromo-2-p-chlorophenyl-5-benzoxazolylacetate (3 g.) in dioxan (30 ml.) was treated with aqueous 2N sodium hydroxide solution. The mixture was acidified and crude α-bromo-2-p-chlorophenyl-5-benzoxazolylacetic acid was filtered off. This solid was dissolved in ethanol (30 ml.) and palladium on charcoal added. The solution was hydrogenated for 3 hours. The catalyst was removed and the solution was evaporated to dryness. The residue was crystallised to give 2-p-chlorophenyl-5-benzoxazolylacetic acid, m.p. 241°-242° C.