Lithium Hydroxide → HCID 118562724, compound

HRID 1501138Notes

Reaction equation

HRID 1501138 reaction equation
[OH-].[Li+].[Br:3][C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][CH:22]=1)[O:7][C@H:8]([C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16]C)=[O:15])=[CH:12][CH:11]=1)[CH3:9]>CO.O>[Br:3][C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][CH:22]=1)[O:7][C@H:8]([C:10]1[CH:19]=[CH:18][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=1)[CH3:9]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 89585110HCID 89585110, compound

Product 1

HCID 118562724HCID 118562724, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Lithium hydroxide (2 g, 83.3 mmol) was added to a solution of (S)-methyl 4-(1-(3-bromophenoxy)ethyl)benzoate (1.8 g, 5.4 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 hydrogen chloride (aq) was added to make pH 2-3, and the product was extracted with dichloromethane. The combined organic phase was washed with Sodium Chloride (aq) (20 mL×3), dried over anhydrous sodium sulfate, and the solvent was evaporated to dryness to give (S)-4-(1-(3-bromophenoxy)ethyl)benzoic acid (1.7 g, 98%).

Workup

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

Sources & evidence

ORD record
ord-933d5066f6314e35ab2d55947e06cc4d
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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