Lithium Hydroxide → 4-(Pentan-2-yl)benzoic acid

HRID 1479752Notes

Reaction equation

HRID 1479752 reaction equation
[OH-].[Li+].[CH3:3][CH:4]([C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][CH:9]=1)[CH2:5][CH2:6][CH3:7]>O1CCCC1.CO.O>[CH3:3][CH:4]([C:8]1[CH:9]=[CH:10][C:11]([C:12]([OH:14])=[O:13])=[CH:16][CH:17]=1)[CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 76779858Methyl 4-(pentan-2-yl)benzoate

Product 1

HCID 2812844-(Pentan-2-yl)benzoic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of lithium hydroxide (121 mg, 2.9 mmol) in tetrahydrofuran, methanol and water (20 mL, 3:1:1, V/V) was added methyl 4-(pentan-2-yl)benzoate (170 mg, 0.58 mmol). The reaction mixture was stirred at room temperature for 1 hour. The mixture was quench with 10% hydrochloric acid aqueous, extracted with dichloromethane and menthol (20 ml, 10:1), the combine organic layer was dried by anhydrous sodium sulfate, filtered and concentrated to give product 4-(pentan-2-yl)benzoic acid as a white yield (160 mg, 99%).

Workup

  1. customThe mixture was quench with 10% hydrochloric acid aqueous
  2. extractionextracted with dichloromethane and menthol (20 ml, 10:1)
  3. dry with materialthe combine organic layer was dried by anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a83ddbc216434115bb003bf20256db56
Source dataset
uspto-grants-2016_08
Patent number
US09409865B2

Reaction notes

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