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

HRID 636511Notes

Reaction equation

HRID 636511 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 ⅓ 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
  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-88c1c8a5f22446ad9b96ce279a86ffae
Source dataset
uspto-grants-2001_02
Patent number
US06194396B1

Reaction notes

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