Hydrochloric Acid → Ethyl 3-methoxy-4-[[(trifluoromethyl)sulfonyl]oxy]benzoate

HRID 2220618Notes

Reaction equation

HRID 2220618 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].[C:16]([O:27][CH2:28][CH3:29])(=[O:26])[C:17]1[CH:25]=[CH:24][C:22](O)=[C:19]([O:20][CH3:21])[CH:18]=1.N1C=CC=CC=1.Cl>C(Cl)Cl.C(OCC)(=O)C>[CH3:21][O:20][C:19]1[CH:18]=[C:17]([CH:25]=[CH:24][C:22]=1[O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])[C:16]([O:27][CH2:28][CH3:29])=[O:26]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 12038Ethyl vanillateHCID 67749Trifluoromethanesulfonic anhydride

Product 1

HCID 22171362Ethyl 3-methoxy-4-[[(trifluoromethyl)sulfonyl]oxy]benzoate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Trifluoromethanesulfonic anhydride (0.944 mL) was added to an ice-cooled mixture of ethyl vanillate (1.00 g) and pyridine (0.454 mL) in methylene chloride (5 mL) with stirring, and the mixture was stirred for 10 minutes. The reaction mixture was poured into a mixture of 1 mol/L hydrochloric acid and ethyl acetate. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/10) to afford ethyl 3-methoxy-4-trifluoromethanesulfonyloxybenzoate (1.467 g).

Workup

  1. temperaturecooled
  2. stirringthe mixture was stirred for 10 minutes
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/10)

Sources & evidence

ORD record
ord-baf8a6bfff3f446092c55d939015b5a1
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

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