Ethanol → 1,3-Benzoxazol-4-ol

HRID 275798Notes

Reaction equation

HRID 275798 reaction equation
Cl.[NH2:2][C:3]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:4]=1[OH:5].O.[CH2:12](O)C>>[OH:10][C:9]1[C:3]2[N:2]=[CH:12][O:5][C:4]=2[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 962WaterHCID 4592471,3-Benzenediol, 2-amino-, hydrochloride (1:1)

Product 1

HCID 137206971,3-Benzoxazol-4-ol

Procedure

2-Aminoresorcinol hydrochloride (2 g) and triethylchloroformate (4.5 ml) were heated to reflux under nitrogen for 3 h. After cooling to room temperature, the reaction mixture was poured into a mixture of water (70 ml) and ethanol (20 ml). The mixture was stirred vigorously for 30 minutes, then left to stand at room temperature overnight. The beige precipitate which formed was collected by filtration, and dried by azeotroping with toluene to give the title compound as a beige solid (1.2 g).

Workup

  1. temperatureto reflux under nitrogen for 3 h
  2. waitleft
  3. waitto stand at room temperature overnight
  4. customThe beige precipitate which formed
  5. filtrationwas collected by filtration
  6. customdried
  7. customby azeotroping with toluene

Sources & evidence

ORD record
ord-88646d822d164a579bb5c38570591b6e
Source dataset
uspto-grants-2002_03
Patent number
US06353010B1

Reaction notes

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