Sodium Iodide → Methyl 4-(cyclopropylmethoxy)benzoate

HRID 1695240Notes

Reaction equation

HRID 1695240 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[Na+].[I-].C([O-])([O-])=O.[K+].[K+].Br[CH2:21][CH:22]1[CH2:24][CH2:23]1>CC(C)=O>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:21][CH:22]2[CH2:24][CH2:23]2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 81503Bromomethylcyclopropane

Product 1

HCID 57589023Methyl 4-(cyclopropylmethoxy)benzoateYield 79%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-hydroxy-benzoic acid methyl ester (2.0 g, 13.1 mmol, 1.2 eq) was dissolved in acetone (20 mL), NaI (0.97 g, 6.5 mmol, 0.5 eq) and K2CO3 (3.0 g, 21.8 mmol, 2.0 eq) were added and the mixture was stirred at room temperature for 20 min. (Bromomethyl)cyclopropane (1.1 mL, 10.3 mmol, 1.0 eq) was added, and the reaction was refluxed for 2 days. The solvent was concentrated under reduced pressure, NaOH 10% was added, and the product was extracted with DCM. The organic phase was dried over Na2SO4 and the solvent evaporated under reduced pressure. The title product (1.23 g, yield 79%) was recovered and used without further purification.

Workup

  1. additionwas added
  2. temperaturethe reaction was refluxed for 2 days
  3. concentrationThe solvent was concentrated under reduced pressure, NaOH 10%
  4. additionwas added
  5. extractionthe product was extracted with DCM
  6. dry with materialThe organic phase was dried over Na2SO4
  7. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-b94f8dbea5464c9a99e038d35417514f
Source dataset
uspto-grants-2012_04
Patent number
US08163729B2

Reaction notes

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