Pyridine → 4-Formyl-2,6-dimethylphenyl trifluoromethanesulfonate

HRID 400253Notes

Reaction equation

HRID 400253 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[CH3:16][C:17]1[CH:18]=[C:19]([C:22](C)=[CH:23][C:24]=1O)[CH:20]=[O:21].N1C=CC=C[CH:28]=1>O>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:24]1[C:23]([CH3:28])=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][C:17]=1[CH3:16])(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 128272904-Hydroxy-2,5-dimethyl-benzaldehyde

Product 1

HCID 544771104-Formyl-2,6-dimethylphenyl trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.3 ml of trifluoromethanesulfonic anhydride were added under an inert gas atmosphere at 0° C., to a mixture of 3.0 g of 3,6-dimethyl-4-hydroxy-benzaldehyde and 20 ml of pyridine and the mixture was stirred for 3 hours at ambient temperature. Then the reaction medium was poured into ice-cooled water and after extraction with dichloromethane, and drying of the organic phase over magnesium sulfate and concentrated to dryness under reduced pressure, the residue was chromatographed on silica, eluting with a cyclohexane/ethyl acetate mixture (9/1) to obtain 4.11 g of the expected product.

Workup

  1. additionThen the reaction medium was poured into ice-
  2. extractionafter extraction with dichloromethane
  3. dry with materialdrying of the organic phase over magnesium sulfate
  4. concentrationconcentrated to dryness under reduced pressure
  5. customthe residue was chromatographed on silica
  6. washeluting with a cyclohexane/ethyl acetate mixture (9/1)

Sources & evidence

ORD record
ord-7901a75e86764659b827d3bc89e89e08
Source dataset
uspto-grants-1998_10
Patent number
US05827887

Reaction notes

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