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

HRID 1626331Notes

Reaction equation

HRID 1626331 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-df096ee646184b8daae230dbc46c38d2
Source dataset
uspto-grants-2014_07
Patent number
US08785449B2

Reaction notes

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