Sodium Hydroxide → 3-Methylbenzo[d]isoxazole-6-carboxylic acid

HRID 2306662Notes

Reaction equation

HRID 2306662 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([O:13]C)=[O:12])=[CH:10][C:5]=2[O:4][N:3]=1.[OH-].[Na+]>CO>[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([OH:13])=[O:12])=[CH:10][C:5]=2[O:4][N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22610095HCID 22610095, compound

Product 1

HCID 226100463-Methylbenzo[d]isoxazole-6-carboxylic acidYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-methyl-1,2-benzisoxazole-6-carboxylate (170 mg, 0.89 mmole) is dissolved in 6 ml MeOH under nitrogen. The solution is treated with 2N aqueous NaOH (1 ml, 2 mmole) and the mixture is stirred 4 h at rt. The volatiles are removed in vacuo and the residue is dissolved in 4 ml water. The pH of the solution is adjusted to 3 with 10% aqueous HCl, the white precipitate is collected, is washed with water, and is dried to give 144 mg (92%) of 3-methyl-1,2-benzisoxazole-6-carboxylic acid as a white solid. MS m/z (ESI): 176.2 (M−H)−.

Workup

  1. customThe volatiles are removed in vacuo
  2. dissolutionthe residue is dissolved in 4 ml water
  3. customthe white precipitate is collected
  4. washis washed with water
  5. customis dried

Sources & evidence

ORD record
ord-b5edccec4cfc443ea80447c37bfbc9dc
Source dataset
uspto-grants-2004_12
Patent number
US06828330B2

Reaction notes

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