Lithium Hydroxide → 7-Hydroxy-2-methyl-5-benzoxazolecarboxylic acid

HRID 1880439Notes

Reaction equation

HRID 1880439 reaction equation
C[O:2][C:3]1[C:11]2[O:10][C:9]([CH3:12])=[N:8][C:7]=2[CH:6]=[C:5]([C:13]([O:15]C)=[O:14])[CH:4]=1.[OH-].[Li+]>C(O)C>[OH:2][C:3]1[C:11]2[O:10][C:9]([CH3:12])=[N:8][C:7]=2[CH:6]=[C:5]([C:13]([OH:15])=[O:14])[CH:4]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 50853152HCID 50853152, compound

Product 1

HCID 669205527-Hydroxy-2-methyl-5-benzoxazolecarboxylic acidYield 69.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 7-methoxy-2-methyl-1,3-benzoxazole-5-carboxylate (365 mg) was dissolved in 16 mL ethanol and 3.3 mL of 1 M lithium hydroxide was added. Reaction was heated at 60° C. overnight. Volatiles were removed under vacuum and the residue dissolved in water and acidified with 1 M HCl to pH3. Collected the tan solid by filtration and washed with water. Air dried to yield 221 mg (65%) of 7-hydroxy-2-methyl-1,3-benzoxazole-5-carboxylic acid LC/MS=208 (M+H).

Workup

  1. customReaction
  2. customVolatiles were removed under vacuum
  3. dissolutionthe residue dissolved in water
  4. customCollected the tan solid
  5. filtrationby filtration
  6. washwashed with water
  7. customAir dried

Sources & evidence

ORD record
ord-17bbec150bd3451c8471c466ad6451ef
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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