Sodium Iodide → Methyl 4-(cyclopropylmethoxy)-3-methoxybenzoate

HRID 1695190Notes

Reaction equation

HRID 1695190 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([O:11][CH3:12])[CH:5]=1.[Na+].[I-].C([O-])([O-])=O.[K+].[K+].Br[CH2:23][CH:24]1[CH2:26][CH2:25]1>CC(C)=O>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:23][CH:24]2[CH2:26][CH2:25]2)=[C:6]([O:11][CH3:12])[CH:5]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 19844Methyl VanillateHCID 81503Bromomethylcyclopropane

Product 1

HCID 67274610Methyl 4-(cyclopropylmethoxy)-3-methoxybenzoateYield 93%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-hydroxy-3-methoxy-benzoic acid methyl ester (1.0 g, 5.5 mmol, 1.0 eq) was dissolved in acetone (14 mL), NaI (0.5 eq) and K2CO3 (1.0 g, 2.0 eq) were added and the mixture was stirred at room temperature for 30 min. (Bromomethyl)cyclopropane (0.53 mL, 0.9 eq) was added, and the mixture was refluxed for 2 days. The solvent was concentrated under reduced pressure, NaOH 10% was added, and it was extracted with DCM and dried. The title product (1.21 g, yield 93%) was recovered and used without further purification.

Workup

  1. additionwas added
  2. temperaturethe mixture was refluxed for 2 days
  3. concentrationThe solvent was concentrated under reduced pressure, NaOH 10%
  4. additionwas added
  5. extractionit was extracted with DCM
  6. customdried

Sources & evidence

ORD record
ord-0d6b2f38e6b74617946332d1f7db7721
Source dataset
uspto-grants-2012_04
Patent number
US08163729B2

Reaction notes

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