Hydrochloric Acid → 3-(3-Chlorophenyl)-5-methyl-1,2-oxazole-4-carboxylic acid

HRID 1897114Notes

Reaction equation

HRID 1897114 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)=[N:8][O:9][C:10]=1[CH3:11])=[O:5])C.[OH-].[Na+].Cl.O>C(O)C>[Cl:18][C:14]1[CH:13]=[C:12]([C:7]2[C:6]([C:4]([OH:5])=[O:3])=[C:10]([CH3:11])[O:9][N:8]=2)[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 10901525Ethyl 3-(3-chlorophenyl)-5-methylisoxazole-4-carboxylate

Product 1

HCID 242595943-(3-Chlorophenyl)-5-methyl-1,2-oxazole-4-carboxylic acidYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-(3-chloro-phenyl)-5-methyl-isoxazole-4-carboxylic acid ethyl ester (9.1 g, 36 mmol) in ethanol (50 mL) was added aqueous sodium hydroxide (4 N, 10 mL). After heating at reflux for 1 h the mixture was cooled to room temperature and acidified with HCl (4 N, 10 mL) and water (10 mL) at 0° C. Purification by filtration and drying afforded the title compound (8.3 g, 97%) which was obtained as a white solid. Mp: 171-173° C.

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 1 h the mixture
  3. customPurification
  4. filtrationby filtration
  5. customdrying

Sources & evidence

ORD record
ord-9c48d1f2ddd543a280ea99dff49cab86
Source dataset
uspto-grants-2013_08
Patent number
US08518974B2

Reaction notes

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