Sodium Hydroxide → 5-Benzoxazoleacetic acid, 2-(4-chlorophenyl)-

HRID 2398747Notes

Reaction equation

HRID 2398747 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]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53740102Methyl alpha-bromo-2-p-chlorophenyl-5-benzoxazolylacetate

Product 1

HCID 30397785-Benzoxazoleacetic acid, 2-(4-chlorophenyl)-

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

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.

Workup

  1. filtrationcrude α-bromo-2-p-chlorophenyl-5-benzoxazolylacetic acid was filtered off
  2. dissolutionThis solid was dissolved in ethanol (30 ml.)
  3. additionpalladium on charcoal added
  4. customThe catalyst was removed
  5. customthe solution was evaporated to dryness
  6. customThe residue was crystallised

Sources & evidence

ORD record
ord-ef576e6f8a8e4fbeb47d5cbf4a4f4bf3
Source dataset
uspto-grants-1977_05
Patent number
US04025636

Reaction notes

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