Potassium Carbonate → methyl (4-cyanophenoxy)acetate

HRID 1807482Notes

Reaction equation

HRID 1807482 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].Br[CH2:11][C:12]([O:14][CH3:15])=[O:13].C([O-])([O-])=O.[K+].[K+]>CC#N>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 130194-CyanophenolHCID 60984Methyl bromoacetate

Product 1

HCID 1506457methyl (4-cyanophenoxy)acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-cyanophenol and methyl bromoacetate in CH3CN was treated with K2CO3 and refluxed for 18 hours. Then the reaction was cooled to room temperature and concentrated. The residue was partitioned between EtOAc and H2O and the organic layer was washed with brine, driend (Na2SO4), filtered and evaporated. Flash chromatography (SiO2, hexanes/EtOAc) gave pure methyl 2-(4-cyanophenoxy)acetate.

Workup

  1. temperaturerefluxed for 18 hours
  2. concentrationconcentrated
  3. customThe residue was partitioned between EtOAc and H2O
  4. washthe organic layer was washed with brine, driend (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-457adbad18f04b6594c2b23ff5febce7
Source dataset
uspto-grants-2013_01
Patent number
US08357699B2

Reaction notes

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