Potassium Carbonate → Methyl 3-(3-methoxypropoxy)-4-methylbenzoate

HRID 1158403Notes

Reaction equation

HRID 1158403 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([OH:11])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:20][CH2:21][CH2:22][O:23][CH3:24]>C(#N)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([O:11][CH2:20][CH2:21][CH2:22][O:23][CH3:24])[CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 354091Methyl 3-hydroxy-4-methylbenzoateHCID 135229891-Iodo-3-methoxypropane

Product 1

HCID 68447108Methyl 3-(3-methoxypropoxy)-4-methylbenzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3-hydroxy-4-methyl-benzoic acid methyl ester (7.7 g, 32.43 mmol), potassium carbonate (6.72 g, 48.65 mmol) and 1-iodo-3-methoxy propane (7.14 g, 35.68 mmol) in acetonitrile (125 mL) is stirred at reflux for 26 h. The solvent is concentrated under reduced pressure, H2O (100 mL) is added, and the aqueous layer is extracted with ether (50 mL×4). The combined organic extracts are washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the title which is used without further purification in the next step. TLC, Rf (hexane/AcOEt 2:1)=0.65. 1H-NMR (CDCl3, 300 MHz): δ=2.10 (p, 2H), 2.3 (s, 3H), 3.38 (s, 3H), 3.62 (t, 2H), 3.9 (s, 3H), 4.15 (t, 2H), 7.15 (d, 1H), 7.45 (s, 1H), 7.55 (d, 1H) ppm.

Workup

  1. temperatureat reflux for 26 h
  2. concentrationThe solvent is concentrated under reduced pressure, H2O (100 mL)
  3. additionis added
  4. extractionthe aqueous layer is extracted with ether (50 mL×4)
  5. washThe combined organic extracts are washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto afford the title which
  9. customis used without further purification in the next step

Sources & evidence

ORD record
ord-03540ff7335a4d6c86d1d5ce324524c7
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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