Hydrochloric Acid → 3-Butyl-isoxazole-4-carboxylic acid

HRID 1807512Notes

Reaction equation

HRID 1807512 reaction equation
C([O:3][C:4]([C:6]1[C:7]([CH2:11][CH2:12][CH2:13][CH3:14])=[N:8][O:9][CH:10]=1)=[O:5])C.O.[OH-].[Li+].CO.Cl>C1COCC1.O>[CH2:11]([C:7]1[C:6]([C:4]([OH:5])=[O:3])=[CH:10][O:9][N:8]=1)[CH2:12][CH2:13][CH3:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 666436613-Butyl-isoxazole-4-carboxylic acid ethyl ester

Product 1

HCID 666435693-Butyl-isoxazole-4-carboxylic acidYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of (E and/or Z)-3-butyl-isoxazole-4-carboxylic acid ethyl ester (10.0 g, 51 mmol) in THF (100 mL) was added a solution of lithium hydroxide monohydrate (4.25 g, 101 mmol) in water (100 mL) and then methanol (100 mL) added and the resulting mixture stirred at room temperature for 1 h. The mixture was acidified to pH 1 with HCl (2 N) and the resulting mixture extracted with ethyl acetate. The combined organic layers were then washed with water and brine, dried over sodium sulphate, filtered and evaporated to afford the title compound (8.33 g, 97%) which was obtained as an off white solid. MS: m/e=168.1 [M−H]+.

Workup

  1. extractionthe resulting mixture extracted with ethyl acetate
  2. washThe combined organic layers were then washed with water and brine
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-a56b568abc7a41b794a13b60d4e8817a
Source dataset
uspto-grants-2013_01
Patent number
US08357703B2

Reaction notes

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