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

HRID 2221626
Notes
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Reaction equation

HRID 2221626 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:23][C:24]([O:26]CC)=[O:25])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[N:12]=[C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:14][C:15]=1[CH3:16].[OH-].[Na+].O1CCCC1.Cl>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:23][C:24]([OH:26])=[O:25])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[N:12]=[C:13]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[O:14][C:15]=1[CH3:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86605738Ethyl {3-methoxy-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl}acetate

Product 1

HCID 69214208{3-Methoxy-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl}acetic acidYield 85.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl {3-methoxy-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl}acetate (10.00 g), 2N aqueous sodium hydroxide solution (40 mL), tetrahydrofuran (100 mL) and ethanol (20 mL) was stirred overnight at room temperature. The reaction mixture was acidified by adding hydrochloric acid and concentrated. The residue was extracted with an ethyl acetate/tetrahydrofuran (1:1, v/v) mixed solvent. The organic layer was washed successively with distilled water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was recrystallized from methanol-diethyl ether to give {3-methoxy-4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl}acetic acid as a white solid (7.92 g, yield 85%). melting point: 176-177° C.

Workup

  1. concentrationconcentrated
  2. extractionThe residue was extracted with an ethyl acetate/tetrahydrofuran (1:1
  3. additionv/v) mixed solvent
  4. washThe organic layer was washed successively with distilled water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was recrystallized from methanol-diethyl ether

Sources & evidence

ORD record
ord-545dac9701c64886a4737fba049be25a
Source dataset
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07368578B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes