Potassium Hydroxide → 1,3-Benzoxazole-7-carboxylic acid

HRID 380522Notes

Reaction equation

HRID 380522 reaction equation
C[O:2][C:3]([C:5]1[C:13]2[O:12][CH:11]=[N:10][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:4].[OH-].[K+]>CO.O>[O:12]1[C:13]2[C:5]([C:3]([OH:4])=[O:2])=[CH:6][CH:7]=[CH:8][C:9]=2[N:10]=[CH:11]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 19771047Methyl benzo[d]oxazole-7-carboxylate

Product 1

HCID 183553101,3-Benzoxazole-7-carboxylic acidYield 88.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 0.21 g (1.18 mmol) of methyl-7-benzoxazole carboxylate in 6 mL of CH3OH at 0° C. was added 2.9 mL of a 1N solution of KOH in water and the reaction mixture was stirred at rt for 1 h. The reaction mixture was partitioned between water and CH2Cl2. The aqueous fraction was made acidic with 1N HCl solution and extracted with CH2Cl2. The organic fraction was dried over Na2SO4, filtered and the filtrate was concentrated to give 0.17 g of the title compound as a yellow solid.

Workup

  1. customThe reaction mixture was partitioned between water and CH2Cl2
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic fraction was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-b96fba2f4bc645568591289279a61574
Source dataset
uspto-grants-2001_10
Patent number
US06303593B1

Reaction notes

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