Sodium Hydroxide → HCID 53665016, compound

HRID 257632Notes

Reaction equation

HRID 257632 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][O:19][C:20]3[CH:21]=[C:22]([CH:26]=[CH:27][C:28]([O:30]C)=[O:29])[CH:23]=[CH:24][CH:25]=3)[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>[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][O:19][C:20]3[CH:21]=[C:22]([CH:26]=[CH:27][C:28]([OH:30])=[O:29])[CH:23]=[CH:24][CH:25]=3)[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

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53704491HCID 53704491, compound

Product 1

HCID 53665016HCID 53665016, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 3-[3-[(4,5-diphenyl-2-oxazolyl)methoxy]phenyl]-2-propenoate (3 g, 7.2 mmol), 5N sodium hydroxide solution (4.40 mL) and methanol (60 mL) was heated to reflux. After 30 minutes, the mixture was cooled, concentrated, diluted with water and acidified to pH=1 with 2N hydrochloric acid solution. A yellow solid was filtered off and recyrstallized from a mixture of hexanes and CH2Cl2 to give 3-[3-[(4,5-diphenyl-2-oxazolyl)methoxy]phenyl]-2-propenoic acid (2.25 g, 77%), mp 145°-147° C.

Workup

  1. temperaturewas heated to reflux
  2. temperaturethe mixture was cooled
  3. concentrationconcentrated
  4. additiondiluted with water
  5. filtrationA yellow solid was filtered off
  6. additionrecyrstallized from a mixture of hexanes and CH2Cl2

Sources & evidence

ORD record
ord-33c5ce22226c41c397d23ed4564a7bea
Source dataset
uspto-grants-1993_11
Patent number
US05262540

Reaction notes

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