Sodium Iodide → HCID 67187037, compound

HRID 1695183Notes

Reaction equation

HRID 1695183 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[CH3:11].[Na+].[I-].C([O-])([O-])=O.[K+].[K+].Br[CH2:22][CH:23]1[CH2:25][CH2:24]1>CC(C)=O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:22][CH:23]2[CH2:25][CH2:24]2)=[CH:6][C:5]=1[CH3:11]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 12351986Methyl 4-hydroxy-2-methylbenzoate

Product 1

HCID 67187037HCID 67187037, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Hydroxy-2-methyl-benzoic acid methyl ester (1.0 g, 6.0 mmol, 1.0 eq) was dissolved in acetone (14 mL), NaI (0.45 g, 3.0 mmol, 0.5 eq) and K2CO3 (1.66 g, 12.0 mmol, 2.0 eq) were added ad the mixture was stirred at room temperature for 20 min. (Bromomethyl)cyclopropane (0.53 mL, 5.4 mmol, 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 the crude was extracted with DCM and dried. 0.42 g of title product (yield 32%) were 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. extractionthe crude was extracted with DCM
  6. customdried

Sources & evidence

ORD record
ord-0fb8cbe1d6d244e5aaabec3f6a4af1ae
Source dataset
uspto-grants-2012_04
Patent number
US08163729B2

Reaction notes

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