Lithium Hydroxide → 3-(5-p-Tolyl-isoxazol-3-yl)-benzoic acid

HRID 2113908Notes

Reaction equation

HRID 2113908 reaction equation
C[O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)[O:12][N:11]=2)[CH:5]=1.[OH-].[Li+]>O1CCOCC1>[C:18]1([CH3:21])[CH:17]=[CH:16][C:15]([C:13]2[O:12][N:11]=[C:10]([C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:22])=[O:2])[CH:14]=2)=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 57907091Methyl 3-(5-p-tolylisoxazol-3-yl)benzoate

Product 1

HCID 579071533-(5-p-Tolyl-isoxazol-3-yl)-benzoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In a 25 ml round flask, 330 mg (1.13 mmol) of 3-[5-p-tolyl-isoxazol-3-yl]-benzoic acid methyl ester is dissolved in 10 ml of dioxane and subsequently 1.69 ml of aqueous lithium hydroxide (1M, 1.69 mmol, 1.5 eq.) are added and the resulting solution stirred for 20 h at room temperature. Then, the dioxane is removed in vacuo, 10 ml of water are added and the pH adjusted to 2 with hydrochloric acid (1M). The precipitate is filtered and dried to yield the title compound as a white solid. Mass spectrum: m/z (M−H)+: 278.2

Workup

  1. customThen, the dioxane is removed in vacuo, 10 ml of water
  2. additionare added
  3. filtrationThe precipitate is filtered
  4. customdried

Sources & evidence

ORD record
ord-591d636e6d83455a96a5761dba17be02
Source dataset
uspto-grants-2008_10
Patent number
US07432293B2

Reaction notes

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