Hydrochloric Acid → 2-Methyl-1,3-benzoxazole-6-carboxylic acid

HRID 2080001Notes

Reaction equation

HRID 2080001 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[CH:13][C:8]2[N:9]=[C:10]([CH3:12])[O:11][C:7]=2[CH:6]=1)=[O:4].[OH-].[Na+].Cl>C(O)C>[CH3:12][C:10]1[O:11][C:7]2[CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:14]=[CH:13][C:8]=2[N:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12157467Methyl 2-methylbenzo[d]oxazole-6-carboxylate

Product 1

HCID 184756892-Methyl-1,3-benzoxazole-6-carboxylic acidYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-methyl-benzoxazole-6-carboxylic acid methyl ester (301 mg, 1.57 mmol) in ethanol (10 mL) was added an aqueous solution of 2N sodium hydroxide (10 mL), and the mixture was stirred for 2 hours at room temperature. 2N Hydrochloric acid was added to the reaction mixture to adjust the pH to 4, and the solution was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, then, evaporated in vacuo, and the title compound (270 mg, 1.52 mmol, 97%) was obtained. This was used in the next reaction without purification.

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-79e6707f8f13459da87d56bb5b048062
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

Loading…