Sodium Iodide → Methyl 4-(benzyloxy)-3,5-dimethoxybenzoate

HRID 1730098Notes

Reaction equation

HRID 1730098 reaction equation
[C:1]([O:14][CH3:15])(=[O:13])[C:2]1[CH:12]=[C:9]([O:10][CH3:11])[C:7]([OH:8])=[C:4]([O:5][CH3:6])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[CH2:24](Cl)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(O)C>[CH3:11][O:10][C:9]1[CH:12]=[C:2]([CH:3]=[C:4]([O:5][CH3:6])[C:7]=1[O:8][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:1]([O:14][CH3:15])=[O:13]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 70164Methyl Syringate

Product 1

HCID 563916Methyl 4-(benzyloxy)-3,5-dimethoxybenzoateYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 21.2 g. of methyl syringate, 15 g. of potassium carbonate, 1 g. of sodium iodide, 70 ml. of 95% ethanol (5% methanol), and 14 g. of benzyl chloride was heated at reflux with stirring for 4 hours. The alcohol was stripped off, ice water added, and the mixture extracted with ether. The ether exxtract was washed with water and the ether stripped off. Benzene was added and stripped to remove traces of water. The residual oil was dissolved in isopropanol, charcoal added, and the mixture filtered. Hexane was added and the solution cooled. A total of 19 g. (63% yield) of methyl 3,5-dimethoxy-4-benzyloxybenzoate, m.p. 62°-65° C., was obtained.

Workup

  1. additionA mixture of 21.2 g
  2. temperatureat reflux
  3. extractionthe mixture extracted with ether
  4. washThe ether exxtract was washed with water
  5. additionBenzene was added
  6. customto remove traces of water
  7. dissolutionThe residual oil was dissolved in isopropanol
  8. additioncharcoal added
  9. filtrationthe mixture filtered
  10. additionHexane was added
  11. temperaturethe solution cooled

Sources & evidence

ORD record
ord-746fbc52772b4391993f128acc815931
Source dataset
uspto-grants-1976_11
Patent number
US03991050

Reaction notes

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