Lithium Hydroxide → HCID 89581536, compound

HRID 1501041Notes

Reaction equation

HRID 1501041 reaction equation
[OH-].[Li+].[C:3]1([CH3:22])[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH:10]([C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18]C)=[O:17])=[CH:14][CH:13]=2)[CH3:11])[CH:4]=1>CO.O>[C:3]1([CH3:22])[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH:10]([C:12]2[CH:13]=[CH:14][C:15]([C:16]([OH:18])=[O:17])=[CH:20][CH:21]=2)[CH3:11])[CH:4]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 89580756HCID 89580756, compound

Product 1

HCID 89581536HCID 89581536, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Lithium hydroxide (54 mg, 2.2 mmol) was added to a solution of methyl 4-(1-(m-tolyloxy)ethyl)benzoate (148 mg, 0.55 mmol) in methanol (100 mL) and water (10 mL). The reaction mixture was stirred at room temperature for 3 hours. After the reaction, the solvent was removed in vacuo. 3 mol/L aqueous hydrogen chloride was added to make pH 2-3, and the product was extracted with dichloromethane (100 mL*3) The combined organic phase was washed with sodium Chloride (20 mL*3), dried over anhydrous sodium sulfate, and the solvent was evaporated to dryness to give 4-(1-(m-tolyloxy)ethyl)benzoic acid (124 mg, 88%).

Workup

  1. customAfter the reaction
  2. customthe solvent was removed in vacuo
  3. addition3 mol/L aqueous hydrogen chloride was added
  4. extractionthe product was extracted with dichloromethane (100 mL*3) The combined organic phase
  5. washwas washed with sodium Chloride (20 mL*3)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-c6af3a0474044eb5be134c86dd4512df
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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