Hydrochloric Acid → Ethyl 5-[2,4-dihydroxy-6-(4-nitrophenoxy)phenyl]isoxazole-3-carboxylate

HRID 880361Notes

Reaction equation

HRID 880361 reaction equation
COC[O:4][C:5]1[CH:10]=[C:9]([O:11]COC)[CH:8]=[C:7]([O:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)[C:6]=1[C:25]1[O:29][N:28]=[C:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:26]=1.Cl>C(O)C.O1CCOCC1>[OH:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]([O:15][C:16]2[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=2)[C:6]=1[C:25]1[O:29][N:28]=[C:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:26]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66759150Ethyl 5-[2,4-bis(methoxymethoxy)-6-(4-nitrophenoxy)phenyl]isoxazole-3-carboxylate

Product 1

HCID 136349751Ethyl 5-[2,4-dihydroxy-6-(4-nitrophenoxy)phenyl]isoxazole-3-carboxylateYield 85.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of ethyl 5-[2,4-bis(methoxymethoxy)-6-(4-nitrophenoxy)phenyl]isoxazole-3-carboxylate (25 g, 52 mmol) in ethanol (150 mL) was added 4 M HCl solution in dioxane at room temperature. The solution was set aside for 5 hours then the solvent was evaporated off and the residue taken up in diethyl ether, to provide the title compound (17.1 g, 83% yield).

Workup

  1. customthe solvent was evaporated off

Sources & evidence

ORD record
ord-de9ad93f9b9e4317af9d952420815634
Source dataset
uspto-grants-2015_03
Patent number
US08993556B2

Reaction notes

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