Sodium Hydroxide → 2-(2,6-Dichlorophenyl)-1,3-benzoxazole-6-carboxylic acid

HRID 1514970Notes

Reaction equation

HRID 1514970 reaction equation
C[O:2][C:3]([C:5]1[CH:21]=[CH:20][C:8]2[N:9]=[C:10]([C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:19])[O:11][C:7]=2[CH:6]=1)=[O:4].[OH-].[Na+]>CCO>[Cl:19][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([Cl:18])[C:12]=1[C:10]1[O:11][C:7]2[CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:21]=[CH:20][C:8]=2[N:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 669656572-(2,6-Dichlorophenyl)-benzooxazole-6-carboxylic acid methyl ester

Product 1

HCID 53271602-(2,6-Dichlorophenyl)-1,3-benzoxazole-6-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(2,6-dichlorophenyl)-benzooxazole-6-carboxylic acid methyl ester (1.6 g) in EtOH (13 mL) was added 4N NaOH aqueous solution (6.2 mL). The reaction was stirred at 80° C. for 0.5 h. The reaction mixture was concentrated, diluted with water, and treated with Et2O. The aqueous layer was acidified with 1N HCl aqueous solution. The precipitate was filtered, washed with water, and dried in vacuo to give 2-(2,6-dichloro-phenyl)-benzooxazole-6-carboxylic acid as a white solid: MS (m/z) 308.0 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with water
  3. additiontreated with Et2O
  4. filtrationThe precipitate was filtered
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-a6e1d48bb0984e01833eba7bdc030ddc
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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