Lithium Hydroxide → 4-(3-Methyl-1,2,4-oxadiazol-5-yl)benzoic acid

HRID 452876Notes

Reaction equation

HRID 452876 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[CH:16]=[CH:15][C:10]([C:11]([O:13]C)=[O:12])=[CH:9][CH:8]=2)[O:4][N:3]=1.[OH-].[Li+]>O1CCOCC1.O.C(O)(C)C>[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[CH:16]=[CH:15][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=2)[O:4][N:3]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 11096067Methyl 4-(3-methyl-1,2,4-oxadiazol-5-yl)benzoate

Product 1

HCID 221101114-(3-Methyl-1,2,4-oxadiazol-5-yl)benzoic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 312751,4-DioxaneSolvent

Procedure

Methyl 4-(3-methyl-1,2,4-oxadiazol-5-yl)benzoate (J. R. Young and R. J. DeVita, Tetrahedron Lett., 1998, 39, 3931) was dissolved in a mixture of dioxan (110 ml), water (70 ml) and isopropanol (30 ml), and lithium hydroxide (1.38 g) was added. The mixture was stirred at room temperature for ca 5 h and then the mixture was acidified to ca pH 4 by addition of Amberlyst 15 H+ resin. The resin was removed by filtration and the filtrate was concentrated in vacuo. The solid white precipitate which was obtained was collected by filtration, washed with water on the filter and dried in vacuo at 40° C. for 48 h to give the title compound (D18) (4.23 g).

Workup

  1. additionwas added
  2. additionby addition of Amberlyst 15 H+ resin
  3. customThe resin was removed by filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe solid white precipitate which was obtained
  6. filtrationwas collected by filtration
  7. washwashed with water on the
  8. filtrationfilter
  9. customdried in vacuo at 40° C. for 48 h

Sources & evidence

ORD record
ord-b6ed52d5640e4f99bdd536a73b3e5f50
Source dataset
uspto-grants-2013_07
Patent number
US08492375B2

Reaction notes

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