Hydrochloric Acid → 2-(benzyloxy)-4-(1H-pyrazol-1-yl)benzoic acid

HRID 454473Notes

Reaction equation

HRID 454473 reaction equation
[OH-].[Na+].[CH2:3]([O:10][C:11]1[CH:20]=[C:19]([N:21]2[CH:25]=[CH:24][CH:23]=[N:22]2)[CH:18]=[CH:17][C:12]=1[C:13]([O:15]C)=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O.Cl>O1CCOCC1.CO.C(OCC)(=O)C>[CH2:3]([O:10][C:11]1[CH:20]=[C:19]([N:21]2[CH:25]=[CH:24][CH:23]=[N:22]2)[CH:18]=[CH:17][C:12]=1[C:13]([OH:15])=[O:14])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 66990761methyl 2-(benzyloxy)-4-(1H-pyrazol-1-yl)benzoate

Product 1

HCID 669908412-(benzyloxy)-4-(1H-pyrazol-1-yl)benzoic acidYield 95.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A 2 mol/L aqueous solution of sodium hydroxide (0.56 mL) was added to a solution mixture of the obtained methyl 2-(benzyloxy)-4-(1H-pyrazol-1-yl)benzoate (0.11 g) in dioxane (1.1 mL) and methanol (1.1 mL), followed by stirring at room temperature for 2 hours. Water was added to the reaction mixture. After adjusting the pH to 3 with 6 mol/L hydrochloric acid, ethyl acetate was added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. Diisopropyl ether and hexane were added to the obtained residue, and the solid substance was collected by filtration to obtain 0.10 g of 2-(benzyloxy)-4-(1H-pyrazol-1-yl)benzoic acid as a white solid.

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. washwashed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. additionDiisopropyl ether and hexane were added to the obtained residue
  7. filtrationthe solid substance was collected by filtration

Sources & evidence

ORD record
ord-5cdfa397ca1e4554b1eda79a38e211ad
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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