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

HRID 1489619Notes

Reaction equation

HRID 1489619 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])#[N:8].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH2:2][C:3]([O:5][CH3:6])=[O:4])#[N:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 119072-HydroxybenzonitrileHCID 60984Methyl bromoacetate

Product 1

HCID 1472933Methyl 2-(2-cyanophenoxy)acetateYield 100%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
25 °C

Procedure

Methyl bromoacetate (1.95 mL, 20 mmol) is added dropwise to a solution of 2-cyanophenol (2.38 g, 20 mmol), and K2CO3 (2.78 g, 20.1 mmol) in acetone (100 mL) stirred under N2 at 25° C. After 24 h, the solid is filtered off and the filtrate is concentrated in vacuo and the residue is dried in a vacuum oven to give methyl 2-(2-cyanophenoxy)ethanoate (3.82 g, 100%) as a beige solid. 1H NMR (DMSO) δ7.76 (1H, dd, J=7.6, 1.7 Hz), 7.64 (1H, dt, Jd =1.6 Hz, Jt =8.0 Hz), 7.20~7.10 (2H, m), 5.04 (2H, brs), 3.70 (3H, s).

Workup

  1. filtrationthe solid is filtered off
  2. concentrationthe filtrate is concentrated in vacuo
  3. customthe residue is dried in a vacuum oven

Sources & evidence

ORD record
ord-3a27bad94d6044238b489993a85c3dfe
Source dataset
uspto-grants-1997_10
Patent number
US05679683

Reaction notes

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