Hydrochloric Acid → 4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzoic Acid

HRID 2221628Notes

Reaction equation

HRID 2221628 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21]C)=[O:20])=[CH:17][CH:16]=1.[OH-].[Na+].O1CCCC1.Cl>CO>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([C:19]([OH:21])=[O:20])=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 11461459Methyl 4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzoate

Product 1

HCID 112782814-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzoic AcidYield 90.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzoate (2.00 g), 1N aqueous sodium hydroxide solution (18.6 mL), tetrahydrofuran (30 mL) and methanol (20 mL) was stirred at room temperature for 2 hrs, and at 50-60° C. for 1 hr. The reaction mixture was acidified by adding 1N hydrochloric acid and concentrated. The residue was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was filtered with diisopropyl ether to give 4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzoic acid as a white solid (1.73 g, yield 85%). Recrystallization from ethyl acetate-diisopropyl ether gave needle crystals. melting point: 190-191° C.

Workup

  1. waitat 50-60° C. for 1 hr
  2. concentrationconcentrated
  3. extractionThe residue was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. filtrationThe residue was filtered with diisopropyl ether

Sources & evidence

ORD record
ord-f3e9d8ecfcfb49e19bb4df080eb78719
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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