Nitric Acid → 3-Methyl-5-isoxazolecarboxylic acid

HRID 1058559Notes

Reaction equation

HRID 1058559 reaction equation
[N+:1]([O-:4])(O)=O.C[C:6](=[O:12])[CH2:7][CH2:8][C:9](=O)[CH3:10].[OH2:13]>>[CH3:10][C:9]1[O:4][N:1]=[C:7]([C:6]([OH:12])=[O:13])[CH:8]=1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 962Water2×HCID 80352,5-Hexanedione

Product 1

HCID 769473-Methyl-5-isoxazolecarboxylic acid

Conditions

Temperature
10 °C

Procedure

A solution of 65 g of nitric acid in 77 ml of water is heated to reflux and 25 g of acetonylacetone 9 is added at a rate to maintain reflux. After the addition is complete, reflux is continued for an additional 2 hours. The mixture is cooled to 10 degrees C. and diluted with 77 ml of water to precipitate isoxazole acid 8, which is filtered, washed with 25 ml of water and vacuum dried at 60 degrees C. to afford 15 g of 5-Methyl-3-isoxazolecarboxylic acid 8.

Workup

  1. temperatureto reflux
  2. temperatureto maintain
  3. temperaturereflux
  4. additionAfter the addition
  5. temperaturereflux
  6. customto precipitate isoxazole acid 8, which
  7. filtrationis filtered
  8. washwashed with 25 ml of water and vacuum
  9. customdried at 60 degrees C

Sources & evidence

ORD record
ord-63ed923a98774d6bb794191b1203ab5e
Source dataset
uspto-grants-2003_02
Patent number
US06518254B1

Reaction notes

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