Methanol → Methyl 4-methyl-3-(trifluoromethyl)benzoate

HRID 2039979Notes

Reaction equation

HRID 2039979 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:6]([OH:8])=[O:7].S(=O)(=O)(O)O.[CH3:20]O>>[F:1][C:2]([F:13])([F:14])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:6]([O:8][CH3:20])=[O:7]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 27755924-Methyl-3-(trifluoromethyl)benzoic acid

Product 1

HCID 11952921Methyl 4-methyl-3-(trifluoromethyl)benzoateYield 95%

Procedure

A reactor is charged with 1 g (4.9 mmol) of 3-(trifluoromethyl)-4-methylbenzoic acid in 10 ml methanol in the presence of a catalytic amount of sulphuric acid. The mixture is heated for 6 hours at reflux. The solvent is then evaporated under reduced pressure and 100 ml of a saturated sodium bicarbonate solution is added to the mixture. The solution is extracted by 3*30 ml ethyl acetate. The organic phases are combined, dried on sodium sulphate and evaporated under reduced pressure to give the expected product (1 g, 95%).

Workup

  1. temperatureThe mixture is heated for 6 hours
  2. temperatureat reflux
  3. customThe solvent is then evaporated under reduced pressure and 100 ml of a saturated sodium bicarbonate solution
  4. additionis added to the mixture
  5. extractionThe solution is extracted by 3*30 ml ethyl acetate
  6. customdried on sodium sulphate
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-270e4f47af6d4c1fa6090bdccf55c8a8
Source dataset
uspto-grants-2013_11
Patent number
US08580815B2

Reaction notes

Loading…