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

HRID 2221624Notes

Reaction equation

HRID 2221624 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][C:16]1[N:17]=[C:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[O:19][C:20]=1[CH3:21])[C:6]([O:8]CC)=[O:7].[OH-].[Na+].O1CCCC1.Cl>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][C:16]1[N:17]=[C:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[O:19][C:20]=1[CH3:21])[C:6]([OH:8])=[O:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 69216123Ethyl 3-methoxy-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzoate

Product 1

HCID 692176323-Methoxy-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzoic acidYield 44%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 3-methoxy-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzoate (10.00 g), 2N aqueous sodium hydroxide solution (40 mL), tetrahydrofuran (100 mL) and ethanol (40 mL) was stirred overnight at room temperature. The reaction mixture was acidified by adding hydrochloric acid and concentrated. The residue was extracted with a mixed solvent of ethyl acetate/tetrahydrofuran (1:1, v/v). The organic layer was washed successively with distilled water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was recrystallized from ethanol-diisopropyl ether to give 3-methoxy-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]benzoic acid as a white solid (3.93 g, yield 44%). melting point: 219-220° C.

Workup

  1. concentrationconcentrated
  2. extractionThe residue was extracted with a mixed solvent of ethyl acetate/tetrahydrofuran (1:1
  3. washThe organic layer was washed successively with distilled water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was recrystallized from ethanol-diisopropyl ether

Sources & evidence

ORD record
ord-471b7c9157fc4ecfab5447ef38d5c443
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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