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

HRID 530931Notes

Reaction equation

HRID 530931 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

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 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).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-ffa1131e265d4beca6190ef4cd003140
Source dataset
uspto-grants-2016_05
Patent number
US09353111B2

Reaction notes

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