Hydrochloric Acid → Methyl 2,5-dimethyl-4-trifluoromethanesulfonyloxybenzoate

HRID 30743Notes

Reaction equation

HRID 30743 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].O[C:17]1[C:26]([CH3:27])=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[C:19]([CH3:28])[CH:18]=1.N1C=CC=CC=1.Cl>C(Cl)Cl.C(OC(=O)C)C>[CH3:28][C:19]1[CH:18]=[C:17]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])[C:26]([CH3:27])=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 22615980Methyl 4-hydroxy-2,5-dimethylbenzoate

Product 1

HCID 86605503Methyl 2,5-dimethyl-4-trifluoromethanesulfonyloxybenzoateYield 90.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Trifluoromethanesulfonic anhydride (0.27 g) was added to an ice-cooled mixture of methyl 4-hydroxy-2,5-dimethylbenzoate (0.144 g) and pyridine (0.095 g) in methylene chloride (10 mL) with stirring. The mixture was stirred at room temperature for 30 min, and poured into a mixture of ethylacetate and 2 mol/L hydrochloric acid. 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:n-hexane:ethyl acetate=10/1) to afford the title compound (0.226 g).

Workup

  1. temperaturecooled
  2. stirringThe mixture was stirred at room temperature for 30 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:n-hexane:ethyl acetate=10/1)

Sources & evidence

ORD record
ord-1ca620ff2ff340b0a60419aa8d58879a
Source dataset
uspto-grants-2008_09
Patent number
US07423185B2

Reaction notes

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