Dimethylformamide → 2-Methoxy-5-(2-methoxy-ethoxy)-benzoic acid methyl ester

HRID 2230725Notes

Reaction equation

HRID 2230725 reaction equation
O[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.[CH3:14][O:15][CH2:16][CH2:17]Cl.C(=O)([O-])[O-:20].[K+].[K+].CN(C)C=O>C(OCC)(=O)C>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:10]=[C:11]([O:20][CH2:17][CH2:16][O:15][CH3:14])[CH:2]=[CH:3][C:4]=1[O:12][CH3:13]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium Carbonate2×HCID 123162-Chloroethyl methyl ether2×HCID 12532676Methyl 4-hydroxy-2-methoxybenzoate

Product 1

HCID 701476262-Methoxy-5-(2-methoxy-ethoxy)-benzoic acid methyl esterYield 97.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Stir a mixture of methyl 4-hydroxy-2-methoxybenzoate (Danishefsky et al., J. Med. Chem. 1979, 101, 7001-7008, 0.73 g, 4 mmol), 2-chloroethyl methy ether (1 mL, 12 mmol, Aldrich Chemical Company), potassium carbonate (0.55 g, 4.8 mmol) and dimethylformamide (20 mL) at 50° C. overnight. Cool to room temperature, add 2-chloroethyl methy ether (1 mL) and potassium carbonate (1.36 g), and heat with stirring at 70° C. for six hours. Cool and dilute with ethyl acetate, wash with saturated brine, dry (Na2SO4) the organic phase, filter and concentrate the filtrate in vacuo. Vacuum dry the residue overnight at room temperature to afford 0.94 g of 2-methoxy-5-(2-methoxy-ethoxy)-benzoic acid methyl ester.

Workup

  1. temperatureheat
  2. stirringwith stirring at 70° C. for six hours
  3. temperatureCool
  4. washwash with saturated brine
  5. dry with materialdry (Na2SO4) the organic phase
  6. filtrationfilter
  7. concentrationconcentrate the filtrate in vacuo
  8. customVacuum dry the residue overnight at room temperature

Sources & evidence

ORD record
ord-e4b448320f65456989f8308c614139ee
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

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