Ethanol → 3-Phenethyl-5-methyl-isoxazole-4-carboxylic acid

HRID 972079Notes

Reaction equation

HRID 972079 reaction equation
C([O:3][C:4]([C:6]1[C:7]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:8][O:9][C:10]=1[CH3:11])=[O:5])C.[OH-].[K+].C(O)C>O>[CH2:12]([C:7]1[C:6]([C:4]([OH:5])=[O:3])=[C:10]([CH3:11])[O:9][N:8]=1)[CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 538657393-Phenethyl-5-methyl-isoxazole-4-carboxylic acid ethyl ester

Product 1

HCID 136126033-Phenethyl-5-methyl-isoxazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 300 g. (1.30 mole) 3-phenethyl-5-methyl-isoxazole-4-carboxylic acid ethyl ester, 146 g. (1.60 mole) potassium hydroxide 1500 ml. ethanol and 500 ml. water is stirred for 2 hours at room temperature and 2 additional hours at reflux. The ethanol is evaporated in vacuo and the aqueous solution is cooled and acidified with hydrochloric acid. The resulting solid is filtered and washed with water and triturated with methanol to give 3-phenethyl-5-methyl-isoxazole-4-carboxylic acid; m.p. 154° to 156° C.

Workup

  1. additionA mixture of 300 g
  2. temperature2 additional hours at reflux
  3. customThe ethanol is evaporated in vacuo
  4. temperaturethe aqueous solution is cooled
  5. filtrationThe resulting solid is filtered
  6. washwashed with water
  7. customtriturated with methanol

Sources & evidence

ORD record
ord-1a2f739022ca492ebe68cc157dd72dcf
Source dataset
uspto-grants-1979_07
Patent number
US04163057

Reaction notes

Loading…