Sodium Hydroxide → [3-(5-Methyl[1,2,4]oxadiazol-3-yl)phenoxy]-2-phenylacetic acid

HRID 917576Notes

Reaction equation

HRID 917576 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[O:8][N:7]=[C:6]([C:9]2[CH:10]=[C:11]([CH:24]=[CH:25][CH:26]=2)[O:12][CH:13]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:14]([O:16]C)=[O:15])[N:5]=1>CO>[CH3:3][C:4]1[O:8][N:7]=[C:6]([C:9]2[CH:10]=[C:11]([CH:24]=[CH:25][CH:26]=2)[O:12][CH:13]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:14]([OH:16])=[O:15])[N:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12042529Methyl [3-(5-methyl[1,2,4]oxadiazol-3-yl)phenoxy]-2-phenylacetate

Product 1

HCID 12042530[3-(5-Methyl[1,2,4]oxadiazol-3-yl)phenoxy]-2-phenylacetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

30 ml of 1N sodium hydroxide solution are added to a solution of 10.1 g (31.0 mmol) of methyl [3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]-2-phenylacetate in 30 ml of methanol, and the mixture is heated at 80° C. for 3 hours. The reaction mixture is evaporated, 1N HCl is added, and the mixture is extracted with ethyl acetate. The organic phase is dried and evaporated, and the residue is recrystallised from ether, giving [3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]-2-phenylacetic acid as colourless crystals; ESI 311.

Workup

  1. customThe reaction mixture is evaporated
  2. addition1N HCl is added
  3. extractionthe mixture is extracted with ethyl acetate
  4. customThe organic phase is dried
  5. customevaporated
  6. customthe residue is recrystallised from ether

Sources & evidence

ORD record
ord-4fab5a34e6654caf92e73f748cdb8033
Source dataset
uspto-grants-2007_09
Patent number
US07273867B2

Reaction notes

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