Sodium Hydroxide → 4-(4-Methyloxazol-5-yl)benzoic acid

HRID 68761Notes

Reaction equation

HRID 68761 reaction equation
C[O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][CH:13]=[N:12][C:11]=2[CH3:15])=[CH:6][CH:5]=1.[OH-].[Na+]>CO>[CH3:15][C:11]1[N:12]=[CH:13][O:14][C:10]=1[C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:16])=[O:2])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68289577HCID 68289577, compound

Product 1

HCID 682900554-(4-Methyloxazol-5-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-(4-methyl-oxazol-5-yl)-benzoic acid methyl ester (1.50 g), 1 M aqueous NaOH solution (7.00 mL) and methanol (20 mL) is kept at room temperature overnight. The precipitate is filtered off, dissolved in water and neutralized with 4 M HCl. The precipitate is filtered off, dissolved in dichloromethane and a small amount of methanol, and the solution is dried over Na2SO4 and concentrated in vacuo. The residue is triturated with diethylether to afford the title compound. Mass spectrum (ESI+): m/z=204 [M+H]+.

Workup

  1. filtrationThe precipitate is filtered off
  2. dissolutiondissolved in water and neutralized with 4 M HCl
  3. filtrationThe precipitate is filtered off
  4. dissolutiondissolved in dichloromethane
  5. dry with materiala small amount of methanol, and the solution is dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue is triturated with diethylether

Sources & evidence

ORD record
ord-5bd8e7b8bd6e406aaeec05900acc07b0
Source dataset
uspto-grants-2014_09
Patent number
US08822471B2

Reaction notes

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