Lithium Hydroxide → 2-Oxo-2,3-dihydro-1,3-benzoxazole-6-carboxylic acid

HRID 2075410Notes

Reaction equation

HRID 2075410 reaction equation
[O:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]([O:13]CC)=[O:12])=[CH:10][C:4]=2[O:3]1.[Li+].[OH-]>C1COCC1>[O:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]([OH:13])=[O:12])=[CH:10][C:4]=2[O:3]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 15422978Ethyl 2-oxo-2,3-dihydrobenzo[d]oxazole-6-carboxylate

Product 1

HCID 3914722-Oxo-2,3-dihydro-1,3-benzoxazole-6-carboxylic acidYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To ethyl 2-oxo-2,3-dihydrobenzo[d]oxazole-6-carboxylate in THF (20 mL) was added LiOH (2 g in 10 mL water). The mixture was stirred at room temperature for 20 hours. The solvent was evaporated. The residue was taken up in water and acidified with 5 N HCl to pH=5. The solid was recovered by filtration, washing with water, to provide the pure product as a tan solid (1.44 g, 80%). LCMS (API-ES) m/z: 180 (M+H+).

Workup

  1. customThe solvent was evaporated
  2. filtrationThe solid was recovered by filtration
  3. washwashing with water

Sources & evidence

ORD record
ord-dafbbef0906d4338bc9745b8b79aa25a
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

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