Potassium Carbonate → Methyl 3-(methoxymethyl)benzoate

HRID 732008Notes

Reaction equation

HRID 732008 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10]Br)[CH:5]=1.[C:13](=O)([O-])[O-:14].[K+].[K+]>CO.O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][O:14][CH3:13])[CH:5]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 517981Methyl 3-(bromomethyl)benzoate

Product 1

HCID 23080888Methyl 3-(methoxymethyl)benzoateYield 100.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 3-bromomethyl-benzoic acid methyl ester (556 mg, 2.4 mmol) and potassium carbonate (670 mg, 4.9 mmol) in methanol (10 ml) and tetrathydrofuran (10 ml) was heated at 55° C. for 2 h. After cooling, the reaction mixture was diluted with water and then extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated. After drying in vacuo, 3-methoxymethyl-benzoic acid methyl ester (436 mg, quantitative) was isolated as a white solid. 1H NMR (CDCl3), δ (ppm): 8.01 (s, 1H), 7.98 (d, 1H), 7.55 (d, 1H), 7.43 (t, 1H), 4.50 (s, 2H), 3.92 (s, 3H), 3.41 (s, 3H).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customAfter drying in vacuo

Sources & evidence

ORD record
ord-6320c1d21bcd4409a1700c28029a694f
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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