Methyl Salicylate → Methyl 2-(3-iodopropoxy)-benzoate

HRID 2269895

Reaction equation

HRID 2269895 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].C(=O)([O-])[O-].[Na+].[Na+].[I:18][CH2:19][CH2:20][CH2:21]I.C(OCC)(=O)C.CCCCCC>CC(C)=O>[I:18][CH2:19][CH2:20][CH2:21][O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([O:10][CH3:11])=[O:9]

Participants

6

Reactant 4

HCID 4133Methyl SalicylateHCID 10340Sodium Carbonate2×HCID 123141,3-Diiodopropane2×HCID 21226206Ethyl acetate hexane

Product 1

HCID 18333395Methyl 2-(3-iodopropoxy)-benzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Combine methyl salicylate (5.09 g, 33.2 mmol), sodium carbonate (10.56 g, 99.67 mmol), and 1,3-diiodopropane (29.49 g, 99.67 mmol) in acetone (200 mL). Heat to reflux. After 18 hours, add sodium carbonate (10.56 g, 99.67 mmol) and continue to heat at reflux. After 18 hours, add 1,3-diiodopropane (29.49 g, 99.67 mmol) and continue to heat at reflux. After 18 hours. filter the reaction mixture and concentrate the filtrate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 1/10 ethyl acetate/hexane to give the title compound: Rf=0.29 (silica gel, 1/10 ethyl acetate/hexane).

Workup

  1. temperatureHeat to reflux
  2. temperatureto heat
  3. temperatureat reflux
  4. waitAfter 18 hours
  5. temperatureto heat
  6. temperatureat reflux
  7. waitAfter 18 hours
  8. filtrationfilter the reaction mixture
  9. concentrationconcentrate the filtrate in vacuo
  10. customto give a residue

Sources & evidence

ORD record
ord-f75a37c539eb41af931f147e96adde1a
Source dataset
uspto-grants-2001_12
Patent number
US06329392B1

Linked notes

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