Hydrochloric Acid → 5-[2,4-Bis(benzyloxy)-6-(4-nitrophenoxy)phenyl]isoxazole-3-carboxylic acid

HRID 880354Notes

Reaction equation

HRID 880354 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[C:11]([O:23][C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=2)[C:10]=1[C:33]1[O:37][N:36]=[C:35]([C:38]([O:40]CC)=[O:39])[CH:34]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].Cl>C(O)C.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[C:11]([O:23][C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=2)[C:10]=1[C:33]1[O:37][N:36]=[C:35]([C:38]([OH:40])=[O:39])[CH:34]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 66759309HCID 66759309, compound

Product 1

HCID 667591895-[2,4-Bis(benzyloxy)-6-(4-nitrophenoxy)phenyl]isoxazole-3-carboxylic acidYield 86%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of ethyl 5-[2,4-bis(benzyloxy)-6-(4-nitrophenoxy)phenyl]isoxazole-3-carboxylate (5 g, 9 mmol) in ethanol (150 mL) was added 1.5 M KOH solution (9 mL, 13.5 mmol, 1.5 eq). After stirring for 3 hours at room temperature, 2 M HCl solution (7.5 mL) was added and the suspension taken up in ethyl acetate was washed with brine. After drying and removal of the solvent, the residue was rinsed with a small volume of acetone and filtered off, to give after drying, the title compound (4.1 g, 86% yield).

Workup

  1. washwas washed with brine
  2. customAfter drying
  3. customremoval of the solvent
  4. washthe residue was rinsed with a small volume of acetone
  5. filtrationfiltered off
  6. customto give
  7. customafter drying

Sources & evidence

ORD record
ord-2a07e43fe16f4d81b95eeb3dc07dfeae
Source dataset
uspto-grants-2015_03
Patent number
US08993556B2

Reaction notes

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