Lithium hydroxide, monohydrate → HCID 45117212, compound

HRID 1479739Notes

Reaction equation

HRID 1479739 reaction equation
O.[OH-].[Li+].[CH3:4][CH:5]([CH3:18])[CH:6]([C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][CH:9]=1)[CH3:7]>O1CCCC1.CO.O>[CH3:4][CH:5]([CH3:18])[CH:6]([C:8]1[CH:9]=[CH:10][C:11]([C:12]([OH:14])=[O:13])=[CH:16][CH:17]=1)[CH3:7]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 72291823HCID 72291823, compound

Product 1

HCID 45117212HCID 45117212, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide hydrate (0.42 g, 10 mmol) was added to a solution methyl 4-(3-methylbutan-2-yl)benzoate (0.20 g, 1.0 mmol) in tetrahydrofuran (9 mL), methanol (3 mL) and water (3 mL). The reaction mixture was stirred at room temperature for 3 hours. After the reaction, the solvent was removed in vacuo. Hydrochloric acid (3 mol/L) was added to make pH 1-2, and the product was extracted with dichloromethane (50 mL). The combined organic phase was washed with sodium chloride aqueous solution (20 mL×3), dried over anhydrous sodium sulfate, and the solvent was evaporated to dryness to give pure product 4-(3-methylbutan-2-yl)benzoic acid (0.18 g, 94%) as a white solid.

Workup

  1. customAfter the reaction
  2. customthe solvent was removed in vacuo
  3. additionHydrochloric acid (3 mol/L) was added
  4. extractionthe product was extracted with dichloromethane (50 mL)
  5. washThe combined organic phase was washed with sodium chloride aqueous solution (20 mL×3)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-b499abb9d6a342738b9a58b4d59781c0
Source dataset
uspto-grants-2016_08
Patent number
US09409865B2

Reaction notes

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