Methanol → Methyl 2-methoxy-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepropanoate

HRID 4753Notes

Reaction equation

HRID 4753 reaction equation
[CH3:1]O.[CH3:3][O:4][C:5]1[CH:10]=[C:9]([C:11]([OH:20])([C:16]([F:19])([F:18])[F:17])[C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:7][C:6]=1[CH2:21][CH2:22][C:23]([OH:25])=[O:24].S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[CH3:3][O:4][C:5]1[CH:10]=[C:9]([C:11]([OH:20])([C:16]([F:17])([F:18])[F:19])[C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:7][C:6]=1[CH2:21][CH2:22][C:23]([O:25][CH3:1])=[O:24]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 140766562-Methoxy-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepropanoic acid

Product 1

HCID 14076660Methyl 2-methoxy-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepropanoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 50 ml of methanol in 50 ml toluene are added 7.0 g (0.02 mole) of 2-methoxy-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepropanoic acid and 1 ml of concentrated sulfuric acid. The resulting solution is stirred, heated at reflux for 18 hours, then concentrated to 20 ml at reduced pressure, and extracted with ether. The resulting ether solution is washed with 5% sodium bicarbonate solution and water. The solution is dried with anhydrous magnesium sulfate, filtered and concentrated at reduced pressure to obtain a residual solid which is recrystallized from petroleum ether to give 5.5 g of methyl 2-methoxy-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepropanoate having a melting point of 78°-80°.

Workup

  1. temperatureheated
  2. temperatureat reflux for 18 hours
  3. concentrationconcentrated to 20 ml at reduced pressure
  4. extractionextracted with ether
  5. washThe resulting ether solution is washed with 5% sodium bicarbonate solution and water
  6. dry with materialThe solution is dried with anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated at reduced pressure
  9. customto obtain a residual solid which
  10. customis recrystallized from petroleum ether

Sources & evidence

ORD record
ord-0960a3e8f0f94a8c9c664b1b2f395258
Source dataset
uspto-grants-1988_02
Patent number
US04727180

Reaction notes

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