Methyl iodide → HCID 59214249, compound

HRID 552833Notes

Reaction equation

HRID 552833 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH:13]([CH3:18])[C:14]([F:17])([F:16])[F:15])[C:6]([OH:8])=[O:7])=[O:2].[C:19]([O-])([O-])=O.[K+].[K+].IC>CC(C)=O.O>[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH:13]([CH3:18])[C:14]([F:16])([F:15])[F:17])[C:6]([O:8][CH3:19])=[O:7])=[O:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 59214195HCID 59214195, compound

Product 1

HCID 59214249HCID 59214249, compoundYield 23.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of 3-formyl-4-(2,2,2-trifluoro-1-methylethoxy)benzoic acid (490 mg) and K2CO3 (387 mg) in acetone (10 ml) was added iodomethane (350 μl) at room temperature, followed by stirring for 2 hours. The reaction mixture was diluted with water (15 ml), and extracted with EtOAc (30 ml). The organic layer was dried over anhydrous MgSO4, and filtered to remove the desiccant, and the solvent was concentrated. The residue was purified by silica gel column chromatography (n-hexane:EtOAc=95:5 to 80:20) to obtain methyl 3-formyl-4-(2,2,2-trifluoro-1-methylethoxy)benzoate (122 mg) as a white solid.

Workup

  1. extractionextracted with EtOAc (30 ml)
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. customto remove the desiccant, and the solvent
  5. concentrationwas concentrated
  6. customThe residue was purified by silica gel column chromatography (n-hexane:EtOAc=95:5 to 80:20)

Sources & evidence

ORD record
ord-664f4b2afed448e795874d0355ef77f0
Source dataset
uspto-grants-2011_05
Patent number
US07951825B2

Reaction notes

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