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

HRID 2295915Notes

Reaction equation

HRID 2295915 reaction equation
[OH-:1].[Na+].Cl[C:4](Cl)(Cl)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:7]=1.S(=O)(=O)(O)O.[CH3:23][OH:24]>ClCCl.O>[F:13][C:12]([F:15])([F:14])[C:8]1[CH:7]=[C:6]([CH2:5][C:4]([O:24][CH3:23])=[O:1])[CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 887Methanol2×HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 132558021,1,1-Trichloro-2-(3-trifluoromethylphenyl)ethane

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A 3.36 g. portion of flaked sodium hydroxide was slurried in 33 ml. of methanol and 1 ml. of water, and the mixture was warmed to dissolve most of the base. It was then cooled to ambient temperature and to it was added over 2-3 minutes 4 g. of 1,1,1-trichloro-2-(3-trifluoromethylphenyl)ethane. The mixture was then stirred under reflux at 70° for 4 hours, and was then cooled to 5°. To it was added about 3 ml. of concentrated sulfuric acid. A little more methanol was added to increase the fluidity of the mixture, and the mixture was stirred under reflux again for 45 minutes more. It was then cooled to ambient temperature, and diluted with about 60 ml. of water. A 35 ml. portion of dichloromethane was added, the layers were separated, and the aqueous layer was extracted with three 25 ml. portions of dichloromethane. All of the organics were combined and washed twice with 15 ml. portions of water, dried over sodium sulfate and concentrated to dryness under vacuum to obtain 2.75 g. of product, found to be 80% pure by vapor phase chromatography.

Workup

  1. dissolutionto dissolve most of the base
  2. additionwas added over 2-3 minutes 4 g
  3. temperatureunder reflux at 70° for 4 hours
  4. temperaturewas then cooled to 5°
  5. additionTo it was added about 3 ml
  6. temperatureto increase the fluidity of the mixture
  7. stirringthe mixture was stirred
  8. temperatureunder reflux again for 45 minutes more
  9. temperatureIt was then cooled to ambient temperature
  10. additiondiluted with about 60 ml
  11. customthe layers were separated
  12. extractionthe aqueous layer was extracted with three 25 ml
  13. washwashed twice with 15 ml
  14. dry with materialportions of water, dried over sodium sulfate
  15. concentrationconcentrated to dryness under vacuum
  16. customto obtain 2.75 g

Sources & evidence

ORD record
ord-5dcfeba0957e486485cd40a11278be8c
Source dataset
uspto-grants-1984_01
Patent number
US04426536

Reaction notes

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