Potassium Carbonate → Methyl 2-(2-cyanophenoxy)acetate

HRID 540346Notes

Reaction equation

HRID 540346 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][C:18]([O:20][CH3:21])=[O:19]>CC(C)=O>[C:4]([C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[O:1][CH2:17][C:18]([O:20][CH3:21])=[O:19])#[N:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 119072-HydroxybenzonitrileHCID 60984Methyl bromoacetate

Product 1

HCID 1472933Methyl 2-(2-cyanophenoxy)acetateYield 61.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To the mixture of 2-hydroxybenzonitrile (40 g, 0.34 mol) and potassium carbonate (51.6 g, 0.374 mol) in 850 mL of acetone was added methyl bromoacetate (51.7 g, 0.34 mol) slowly at room temperature. After being stirred at room temperature overnight, the solid was filtered off. The filtrate was concentrated under reduced pressure and the residue was dissolved in ethyl acetate. The organic layer was washed with water then brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to give a residue which was recrystallized in methanol to give 40 g of product as a white solid.

Workup

  1. filtrationthe solid was filtered off
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialbrine, dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a residue which
  9. customwas recrystallized in methanol

Sources & evidence

ORD record
ord-fd675ce6c38641f58bafe201b6bda07b
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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