4-Hydroxybenzoic Acid → 4-(3-Methyl-1,2,4-oxadiazol-5-yl)phenol

HRID 423274

Reaction equation

HRID 423274 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.C([N:18]1[CH:22]=[CH:21]N=C1)(N1C=CN=C1)=O.O[NH:24]C(=O)C>C(OCC)(=O)C.C1COCC1.C1(C)C=CC=CC=1>[CH3:21][C:22]1[N:18]=[C:6]([C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:10][CH:9]=2)[O:8][N:24]=1

Participants

7

Reactant 3

HCID 1354-Hydroxybenzoic AcidHCID 1990Acetohydroxamic AcidHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 36924074-(3-Methyl-1,2,4-oxadiazol-5-yl)phenolYield 10.3%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixed solution of 4-hydroxybenzoic acid (1.0 g) in a mixed solution (15 mL) of toluene and THF (toluene:THF=2:1, v/v) was added carbonyldiimidazole (1.29 g), and the mixture was stirred at room temperature for 1 hour. Subsequently, N-hydroxyacetamide (644 mg) was added thereto, and the mixture was further heated at 150° C. for 2 hours under reflux. The reaction solution was allowed to stand for cooling down to room temperature, diluted with ethyl acetate, washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:1, v/v) to give the title compound (132 mg).

Workup

  1. temperaturethe mixture was further heated at 150° C. for 2 hours
  2. temperatureunder reflux
  3. temperaturefor cooling down to room temperature
  4. washwashed successively with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on silica gel (ethyl acetate

Sources & evidence

ORD record
ord-5f29a971bc74401da4bee98c45b8b125
Source dataset
uspto-grants-2012_01
Patent number
US08101774B2

Linked notes

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