Vanillin → 4-Formyl-2-methoxyphenyl trifluoromethanesulfonate

HRID 1186976Notes

Reaction equation

HRID 1186976 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[F:18][C:19]([F:34])([F:33])[S:20](OC1C=CC([N+]([O-])=O)=CC=1)(=[O:22])=[O:21].CCOC(C)=O>CN(C=O)C>[F:18][C:19]([F:34])([F:33])[S:20]([O:9][C:8]1[CH:10]=[CH:11][C:3]([CH:2]=[O:1])=[CH:4][C:5]=1[O:6][CH3:7])(=[O:22])=[O:21]

Participants

6

Reactant 4

HCID 1183VanillinHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 5498704-Nitrophenyl trifluoromethanesulfonate

Product 1

HCID 108029624-Formyl-2-methoxyphenyl trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of vanillin (20.0 g, 131 mmol) in DMF (200 mL) at room temperature was added potassium carbonate (36 g, 263 mmol) and 4-nitrophenyl trifluoromethanesulfonate (54.0 g, 197 mmol) and the reaction mixture was stirred for 8 h. EtOAc (600 mL) was added to the reaction mixture and the organic layer was washed three times with water, dried, filtered, and concentrated. The crude compound was then purified by flash chromatography (ethylacetate/hexanes 1:9→3:7) to provide 4-formyl-2-methoxyphenyl trifluoromethanesulfonate.

Workup

  1. washthe organic layer was washed three times with water
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude compound was then purified by flash chromatography (ethylacetate/hexanes 1:9→3:7)

Sources & evidence

ORD record
ord-99675710826f444084d85dfa532145c9
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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