Acetyl chloride → 2-Allyl-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenol

HRID 861430Notes

Reaction equation

HRID 861430 reaction equation
[C:1](Cl)(=O)[CH3:2].[CH2:5]([C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=1[OH:18])[C:11](=[N:13][OH:14])[NH2:12])[CH:6]=[CH2:7]>N1C=CC=CC=1>[CH2:5]([C:8]1[CH:9]=[C:10]([C:11]2[N:12]=[C:1]([CH3:2])[O:14][N:13]=2)[CH:15]=[CH:16][C:17]=1[OH:18])[CH:6]=[CH2:7]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 136087609HCID 136087609, compound

Product 1

HCID 1360822352-Allyl-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetyl chloride (2.28 ml) was added dropwise to a solution of 3-allyl-4-hydroxybenzamidoxime (5.4 g) in pyridine (48 ml). The solution was heated at reflux for 16 hours, cooled to ambient temperature and evaporated. The residue was dissolved in ethyl acetate and the solution was washed with saturated aqueous sodium carbonate solution, dried (MgSO4) and evaporated, to give 2-allyl-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenol as a low-melting solid (3.8 g), m/z 217 (M+H).

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 16 hours
  3. customevaporated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthe solution was washed with saturated aqueous sodium carbonate solution
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-7390b4b2ffc34ea8b1fd4bfabde9e5ff
Source dataset
uspto-grants-1998_02
Patent number
US05714496

Reaction notes

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