Ethyl 1,2-benzoxazole-3-carboxylate → 1,2-Benzoxazole-3-carboxylic acid

HRID 1372732Notes

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10]([O:12]CC)=[O:11])=[N:2]1>OS(O)(=O)=O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10]([OH:12])=[O:11])=[N:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

To ethyl benzo(d)isoxazole-3-carboxylate (2.0 g, 10.5 mmol) was added 50 ml of 70% H2SO4. The mixture was heated at 80° C. for 4 hours. The reaction mixture was poured in ice, followed by extraction with ether. The extract was dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent, whereby benzo(d)isoxazole-3-carboxylic acid (980 mg, 57%) was obtained as a colorless solid.

Workup

additionThe reaction mixture was poured in ice
extractionfollowed by extraction with ether
dry with materialThe extract was dried over anhydrous magnesium sulfate
distillationdistilled under reduced pressure
customto remove the solvent

Sources & evidence

ORD record: ord-1f04d93e14ca40de9e48159bed47f2ad
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07157487B2

Reaction notes

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