Methyl Salicylate → Methyl 2-(2,2,2-trifluoroethoxy)benzoate

HRID 1973185Notes

Reaction equation

HRID 1973185 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].FC(F)(F)S(O[CH2:18][C:19]([F:22])([F:21])[F:20])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:20][C:19]([F:22])([F:21])[CH2:18][O:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 4133Methyl SalicylateHCID 11430Potassium CarbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonate

Product 1

HCID 19622905Methyl 2-(2,2,2-trifluoroethoxy)benzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of methyl salicylate (6.4 ml., 7.6 g., 0.05 mole), 2,2,2-trifluoroethyl trifluoromethanesulfonate (13.9 g., 0.06 mole), anhydrous potassium carbonate (13.8 g., 0.1 mole) and acetone (150 ml.) is heated under reflux with efficient stirring for three days. The product is filtered and the filtrate is concentrated to a small volume. It is diluted with cold water and the resulting precipitate is collected and washed successively with cold dilute sodium hydroxide solution and water. The desired material is recrystallized then from aqueous ethanol to afford white solid, m.p. 61-62.

Workup

  1. temperatureis heated
  2. temperatureunder reflux
  3. filtrationThe product is filtered
  4. concentrationthe filtrate is concentrated to a small volume
  5. additionIt is diluted with cold water
  6. customthe resulting precipitate is collected
  7. washwashed successively with cold dilute sodium hydroxide solution and water
  8. customThe desired material is recrystallized
  9. customfrom aqueous ethanol to afford white solid, m.p. 61-62

Sources & evidence

ORD record
ord-ce3af38a9ec54bc6bef429f0e4ade96f
Source dataset
uspto-grants-1976_12
Patent number
US03996280

Reaction notes

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