Water → 1,3-Benzoxazol-5-ol

HRID 240575Notes

Reaction equation

HRID 240575 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]1

Participants

5

Reactant 3

HCID 962WaterHCID 31214Ethyl orthoformateHCID 3017497Aminohydroquinone

Product 1

HCID 190201831,3-Benzoxazol-5-olYield 81%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

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

  1. extractionextracted with ethyl acetate (2×)
  2. washThe organic phase was washed with HCl (2N) and saturated NaHCO3
  3. customdried
  4. 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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