Methanol → Methyl (3-(trifluoromethyl)phenyl)acetate

HRID 2295917Notes

Reaction equation

HRID 2295917 reaction equation
[CH3:1][OH:2].[OH-:3].[K+].Cl[C:6](Cl)(Cl)[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=1.S(=O)(=O)(O)O>ClCCl.O>[F:15][C:14]([F:17])([F:16])[C:10]1[CH:9]=[C:8]([CH2:7][C:6]([O:2][CH3:1])=[O:3])[CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 14797Potassium HydroxideHCID 132558021,1,1-Trichloro-2-(3-trifluoromethylphenyl)ethane

Product 1

HCID 2734603Methyl (3-(trifluoromethyl)phenyl)acetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Seventy ml. of methanol was combined with 10.7 g. of 86% pure potassium hydroxide and the mixture was stirred for 0.5 hour. To it was added 8.0 g. of 1,1,1-trichloro-2-(3-trifluoromethylphenyl)ethane over 3-4 minutes. The mixture was heated and stirred under reflux at 68° for 4.75 hours, cooled to 10° and made acid with 8 ml. of concentrated sulfuric acid. The mixture was then stirred under reflux for 45 minutes more, and cooled to ambient temperature overnight. To it was then added 100 ml. of water and 50 ml. of dichloromethane. The aqueous layer was extracted with two 40 ml. portions of dichloromethane, and the organics were combined, dried over sodium sulfate and concentrated under vacuum to obtain 5.7 g. of brown oil, found to be 96.6% pure product by vapor phase chromatography. The product was further purified by distillation at 70°-73° under 1.3 torr to obtain 4.89 g. of more highly purified product.

Workup

  1. additionTo it was added 8.0 g
  2. temperatureThe mixture was heated
  3. temperatureunder reflux at 68° for 4.75 hours
  4. temperaturecooled to 10°
  5. stirringThe mixture was then stirred
  6. temperatureunder reflux for 45 minutes more
  7. additionTo it was then added 100 ml
  8. extractionThe aqueous layer was extracted with two 40 ml
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated under vacuum
  11. customto obtain 5.7 g
  12. distillationThe product was further purified by distillation at 70°-73° under 1.3 torr
  13. customto obtain 4.89 g

Sources & evidence

ORD record
ord-fef70487296a46538c6c6f682947dbf6
Source dataset
uspto-grants-1984_01
Patent number
US04426536

Reaction notes

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