Acetic Acid → 5-Cyclopropylisoxazole-4-carboxylic acid

HRID 477499Notes

Reaction equation

HRID 477499 reaction equation
[CH:1]1([C:4]2[O:8][N:7]=[CH:6][C:5]=2[C:9]([O:11]CC)=[O:10])[CH2:3][CH2:2]1.C(O)(=O)C.Cl>O>[CH:1]1([C:4]2[O:8][N:7]=[CH:6][C:5]=2[C:9]([OH:11])=[O:10])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 14819891Ethyl 5-cyclopropylisoxazole-4-carboxylate

Product 1

HCID 148198925-Cyclopropylisoxazole-4-carboxylic acidYield 82.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 5-cyclopropylisoxazole-4-carboxylate (203.0 g, 1.12 mole) [prepared in Step B]was added to a solution of 405 ml of glacial acetic acid plus 505 ml of 6 N HCl and the mixture was heated in an oil bath a 105°-110° C. for 3 h. After 18 h at ambient temperature the thick mixture was diluted with water, cooled in an ice bath and filtered to give 140.8 g of the title acid. Recrystallization of an aliquot from acetonitrile gave an analytical sample, mp 163°-165° C.

Workup

  1. temperaturethe mixture was heated in an oil bath a 105°-110° C. for 3 h
  2. temperaturecooled in an ice bath
  3. filtrationfiltered

Sources & evidence

ORD record
ord-a4f323730f214bdcab3d31a32f1d9cbf
Source dataset
uspto-grants-1989_12
Patent number
US04888357

Reaction notes

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