Hydrochloric Acid → 6-Hydroxybenzo[d]oxazole-2-carboxylic acid

Reaction equation

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

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 14798Sodium Hydroxide

HCID 57951073Methyl 6-hydroxybenzo[d]oxazole-2-carboxylate

Product 1

HCID 579510576-Hydroxybenzo[d]oxazole-2-carboxylic acidYield 89.3%

Procedure

A mixture of methyl 6-hydroxybenzo[d]oxazole-2-carboxylate (0.19 g, 1 mmol) and 1N aqueous sodium hydroxide (2 mL) was stirred at room temperature overnight. The reaction mixture was then acidified with concentrated hydrochloric acid. The precipitate was filtered, washed with water, and dried under reduced pressure to afford 6-hydroxybenzo[d]oxazole-2-carboxylic acid as a white solid (0.16 g, 88%). 1H-NMR (DMSO-d6, 300 MHz): δ 10.17 (s, 1H), 7.66 (m, 1H), 7.08 (m, 1H), 6.92 (m, 1H) ppm; MS (ESI): 180.1 (M+1).