Lithium Hydroxide → 2-Chloro-4-(3-methyl-1H-pyrazol-1-yl)benzoic acid

HRID 1635874Notes

Reaction equation

HRID 1635874 reaction equation
C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[CH:13][C:12]([CH3:15])=[N:11]2)=[CH:6][C:5]=1[Cl:16].[OH-].[Li+]>O1CCCC1>[Cl:16][C:5]1[CH:6]=[C:7]([N:10]2[CH:14]=[CH:13][C:12]([CH3:15])=[N:11]2)[CH:8]=[CH:9][C:4]=1[C:3]([OH:17])=[O:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 10634466Methyl 2-chloro-4-(3-Methyl-1H-pyrazol-1-yl)benzoate

Product 1

HCID 108474542-Chloro-4-(3-methyl-1H-pyrazol-1-yl)benzoic acidYield 78.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-chloro-4-(3-methyl-1H-pyrazol-1-yl)-benzoic acid methyl ester (1,42 g) from Example 96 and 6 ml of 1 M aqueous lithium hydroxide in tetrahydrofuran (20 ml) was stirred for 18 hours at room temperature. The reaction mixture was partitioned between ethyl acetate and 1 N hydrochloric acid. The organic layer was washed with water, brine and was dried over anhydrous sodium sulfate. Evaporation of the solvent in vacuo afforded 1.05 g of the title compound as a colorless solid. m.p. 192-193° C. MS (EI), m/z: 236/238 (M)+.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and 1 N hydrochloric acid
  2. washThe organic layer was washed with water, brine
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-3baccd2ebd954e2aa3263ed24e177c55
Source dataset
uspto-grants-2003_01
Patent number
US06511974B1

Reaction notes

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