Lithium hydroxide, monohydrate → 4-(1H-pyrazol-1-yl)benzoic acid

HRID 2244279Notes

Reaction equation

HRID 2244279 reaction equation
[N:1]1([C:6]2[CH:15]=[CH:14][C:9]([C:10]([O:12]C)=[O:11])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.O.[OH-].[Li+]>CO.O>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([C:10]([OH:12])=[O:11])=[CH:14][CH:15]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 972639Methyl 4-(1H-pyrazol-1-yl)benzoate

Product 1

HCID 7365274-(1H-pyrazol-1-yl)benzoic acidYield 97.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 4-(1H-pyrazol-1-yl)benzoate of Step A (0.529 g, 2.62 mmol) in methanol (20 mL) and water (4 mL) was added lithium hydroxide monohydrate (0.220 g, 5.23 mmol) and the reaction mixture heated to reflux for 2 hours. The cooled reaction mixture was concentrated in vacuo to remove methanol and then diluted with water (40 mL). The resulting aqueous solution was washed with diethyl ether (40 mL), then acidified to pH 3 by the addition of concentrated hydrochloric acid. The solid product was filtered and dried in vacuo at 50° C. overnight to afford the title compound (0.479 g, 97%) as a white solid, m.p. 270-272° C.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux for 2 hours
  3. customThe cooled reaction mixture
  4. concentrationwas concentrated in vacuo
  5. customto remove methanol
  6. additiondiluted with water (40 mL)
  7. washThe resulting aqueous solution was washed with diethyl ether (40 mL)
  8. additionacidified to pH 3 by the addition of concentrated hydrochloric acid
  9. filtrationThe solid product was filtered
  10. customdried in vacuo at 50° C. overnight

Sources & evidence

ORD record
ord-10bf5d3205d447e3a74ea85a1df7d5e4
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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