Hydrochloric Acid → 7-Hydroxy-3-methyl-1,3-benzoxazol-2(3H)-one

HRID 2287587Notes

Reaction equation

HRID 2287587 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11]C3CCCCO3)[C:5]=2[O:4][C:3]1=[O:18].Cl>CO>[OH:11][C:10]1[C:5]2[O:4][C:3](=[O:18])[N:2]([CH3:1])[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15588674HCID 15588674, compound

Product 1

HCID 155886757-Hydroxy-3-methyl-1,3-benzoxazol-2(3H)-oneYield 88.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 3-methyl-7-(tetrahydropyran-2-yloxy)-2(3H)-benzoxazolone (280 mg) in methanol (2.3 ml) was added 1N hydrochloric acid (0.5 ml) at ambient temperature, and the mixture was stirred for 30 minutes. The reaction mixture was concentrated to 1/3 volume, and water was added thereto. The mixture was extracted with chloroform, and the extract was dried over magnesium sulfate and concentrated in vacuo. The residue was crystallized with diisopropyl ether to give 7-hydroxy-3-methyl-2(3H)-benzoxazolone (164 mg).

Workup

  1. concentrationThe reaction mixture was concentrated to 1/3 volume, and water
  2. additionwas added
  3. extractionThe mixture was extracted with chloroform
  4. dry with materialthe extract was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was crystallized with diisopropyl ether

Sources & evidence

ORD record
ord-4b7be03da358445d90d580601670e749
Source dataset
uspto-grants-2000_07
Patent number
US06083961

Reaction notes

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