Sodium Hydroxide → 4-(4,5-Dimethyloxazol-2-yl)benzoicacid

HRID 1470644Notes

Reaction equation

HRID 1470644 reaction equation
C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]([CH3:16])=[C:13]([CH3:15])[N:14]=2)=[CH:6][CH:5]=1.[OH-].[Na+]>C1COCC1>[CH3:15][C:13]1[N:14]=[C:10]([C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:17])=[O:2])=[CH:5][CH:6]=2)[O:11][C:12]=1[CH3:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58073807HCID 58073807, compound

Product 1

HCID 282935474-(4,5-Dimethyloxazol-2-yl)benzoicacidYield 65.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-(4,5-dimethyl-oxazol-2-yl)-benzoic acid methyl ester (0.5 g, 2.1 mmol) in THF (20 mL), an aq. solution of 5 N sodium hydroxide (10 mL) was added. The reaction mixture refluxed at 90° C. over night. THF was removed completely under reduced pressure and the residue was acidified with conc. HCl, then E extracted with ethyl acetate (50 mL×2). The combined organic layers were washed with water (25 mL×2) and with brine, then dried over anhydrous sodium sulphate and concentrated to get the title compound (0.3 g, 63.8%).

Workup

  1. customTHF was removed completely under reduced pressure
  2. extractionE extracted with ethyl acetate (50 mL×2)
  3. washThe combined organic layers were washed with water (25 mL×2) and with brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c3919cd25bc44dd8bbeee772308c1649
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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