Potassium Carbonate → Benzoic acid, 3-cyano-5-(2-methoxyethoxy)-, methyl ester

HRID 2216762Notes

Reaction equation

HRID 2216762 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([OH:13])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])#[N:2].C(=O)([O-])[O-].[K+].[K+].[CH3:20][O:21][CH2:22][CH2:23]Cl>CN(C)C=O.C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([O:13][CH2:23][CH2:22][O:21][CH3:20])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])#[N:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 123162-Chloroethyl methyl etherHCID 21942421Methyl 3-cyano-5-hydroxybenzoate

Product 1

HCID 21942473Benzoic acid, 3-cyano-5-(2-methoxyethoxy)-, methyl esterYield 93.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of methyl 3-cyano-5-hydroxybenzoate (302 mg, 1.7 mmol), potassium carbonate (471 mg, 3.4 mmol) and 2-chloroethyl methyl ether (309 μL mg, 3.4 mmol) in N,N-dimethylformamide (4 mL) was heated in a sealed vial at 140° C. for 15 minutes. The reaction was cooled, diluted with ethyl acetate, washed with water and saturated brine, filtered and concentrated. Filtration through silica gel using dichloromethane afforded 375 mg (93%) of methyl 3-cyano-5-(2-methoxyethoxy)benzoate.

Workup

  1. temperatureThe reaction was cooled
  2. washwashed with water and saturated brine
  3. filtrationfiltered
  4. concentrationconcentrated
  5. filtrationFiltration through silica gel

Sources & evidence

ORD record
ord-e3309a59476546c28058ad55f5138083
Source dataset
uspto-grants-2006_09
Patent number
US07112595B2

Reaction notes

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