Water → 1,3-Benzoxazol-5-ol
Reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[OH:9].O.[CH2:11](OC(OCC)OCC)C>Cl>[O:9]1[C:3]2[CH:4]=[CH:5][C:6]([OH:8])=[CH:7][C:2]=2[N:1]=[CH:11]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
To a solution of 2-aminobenzene-1,4-diol (2.40 g, 19.2 mmol) in triethylorthoformate (10 mL) was added 3 drops of concentrated HCl. After heating to 65° C. for 30 minutes and stirring at room temperature for 16 hours, the mixture was poured into water and extracted with ethyl acetate (2×). The organic phase was washed with HCl (2N) and saturated NaHCO3, dried, and concentrated under reduced pressure to provide the product (2.09 g, 81%) as red-black solid.
Workup
- extractionextracted with ethyl acetate (2×)
- washThe organic phase was washed with HCl (2N) and saturated NaHCO3
- customdried
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-3e4198017bb2434cb520e6b73c6ce072
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08648087B2
Reaction notes
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