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

HRID 30744

Reaction equation

HRID 30744 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 (0.94 mL) was added to an ice-cooled mixture of ethyl vanillate (1.0 g) and pyridine (0.45 mL) in methylene chloride (5 mL) with stirring. The mixture was stirred for 10 min, and 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 (1.47 g).

Workup

  1. temperaturecooled
  2. stirringThe mixture was stirred for 10 min
  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-178c977206fe4786a5e3c897eb1be400
Source dataset
uspto-grants-2008_09
Patent number
US07423185B2

Linked notes

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