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Hydrochloric Acid → 4,5-Diphenyl-2-oxazoleoctanoic Acid

HRID 257619
Notes
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Reaction equation

HRID 257619 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27]C)=[O:26])[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].CO.Cl>O>[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])[O:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 15232721Methyl 4,5-diphenyl-2-oxazoleoctanoate

Product 1

HCID 99759574,5-Diphenyl-2-oxazoleoctanoic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent
2×

Procedure

A mixture of methyl 4,5-diphenyl-2-oxazoleoctanoate (7.00 g, 18.5 mmol), 5N sodium hydroxide solution (7.42 mL), water (100 mL) and methanol (20 mL) was heated on a steam bath for 45 minutes. After stirring at room temperature for 75 minutes, the mixture was diluted with water (150 mL), heated on a steam bath for 10 minutes and then allowed to stir overnight at room temperature. The mixture was heated to reflux for 1 hour, cooled, acidified with 2N hydrochloric acid solution and extracted with CH2Cl2. The combined extracts were dried over sodium sulfate and concentrated in vacuo to give an oil that crystallized. Recrystallization from a mixture of diethyl ether, CH2Cl2 and hexanes furnished 4,5-diphenyl-2-ozazoleoctanoic acid (5.25 g, 77%), m.p. 70°-73° C.

Workup

  1. temperaturewas heated on a steam bath for 45 minutes
  2. temperatureheated on a steam bath for 10 minutes
  3. stirringto stir overnight at room temperature
  4. temperatureThe mixture was heated
  5. temperatureto reflux for 1 hour
  6. temperaturecooled
  7. extractionextracted with CH2Cl2
  8. dry with materialThe combined extracts were dried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customto give an oil
  11. customthat crystallized
  12. customRecrystallization
  13. additionfrom a mixture of diethyl ether, CH2Cl2 and hexanes
  14. customfurnished 4,5-diphenyl-2-ozazoleoctanoic acid (5.25 g, 77%), m.p. 70°-73° C.

Sources & evidence

ORD record
ord-95564d5254164aafbecc5274cc70d4a3
Source dataset
uspto-grants-1993_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05262540

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes