Hydrochloric Acid → 3-Ethoxy-1,2-oxazole-5-carboxylic acid

HRID 581101Notes

Reaction equation

HRID 581101 reaction equation
[CH2:1]([O:3][C:4]1[CH:8]=[C:7]([C:9]([O:11]C)=[O:10])[O:6][N:5]=1)[CH3:2].Cl>[OH-].[Na+]>[CH2:1]([O:3][C:4]1[CH:8]=[C:7]([C:9]([OH:11])=[O:10])[O:6][N:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15007417Methyl 3-ethoxy-5-isoxazolecarboxylate

Product 1

HCID 150074183-Ethoxy-1,2-oxazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A stirred solution of methyl 3-ethoxy-5-isoxazolecarboxylate, prepared according to Example 78, (3.00 g, 17.53 mmole) in 75 ml of 2N sodium hydroxide was stirred at room temperature for ten minutes, cooled in an icebath and acidified to pH 3 with concentrated hydrochloric acid. The precipitated solid was collected by filtration. The remaining desired product was isolated by saturating the aqueous filtrate with solid sodium chloride and extracting with ethyl acetate (3×100 ml). A total of 2.46 g (89% yield) of title compound was obtained in this way. The sample was recrystallized from acetonitrile, m.p. 210-13° C.

Workup

  1. temperaturecooled in an icebath
  2. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-c06a4f746390429587d9a1d5b5baa881
Source dataset
uspto-grants-1999_07
Patent number
US05919809

Reaction notes

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