Hydrochloric Acid → 3-Methyl-1,2-benzoxazol-4-ol

HRID 527513Notes

Reaction equation

HRID 527513 reaction equation
C(O[N:5]=[C:6]([C:8]1[C:13]([OH:14])=[CH:12][CH:11]=[CH:10][C:9]=1[OH:15])[CH3:7])(=O)C.Cl>N1C=CC=CC=1>[CH3:7][C:6]1[C:8]2=[C:13]([OH:14])[CH:12]=[CH:11][CH:10]=[C:9]2[O:15][N:5]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 1363786471-(2,6-dihydroxyphenyl)ethanone O-acetyloxime2×

Product 1

HCID 1354299403-Methyl-1,2-benzoxazol-4-olYield 44%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 1-(2,6-dihydroxyphenyl)ethanone O-acetyloxime (Intermediate 9, 437 mg) pyridine (4.0 ml) was added and the reaction mixture was stirred at reflux for 2 hours. After the addition of HCl (4.0 ml of a 5M aqueous solution), the mixture was extracted 3 times with Et2O and the collected organic layers were washed with HCl (1M, aqueous solution). The organic phase was dried over sodium sulphate and filtered. Evaporation afforded the title compound (137 mg).

Workup

  1. temperatureat reflux for 2 hours
  2. extractionwas extracted 3 times with Et2O
  3. washthe collected organic layers were washed with HCl (1M, aqueous solution)
  4. dry with materialThe organic phase was dried over sodium sulphate
  5. filtrationfiltered
  6. customEvaporation

Sources & evidence

ORD record
ord-adb870abfde14683b2b7cbd03bf0518f
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

Loading…