Sodium Hydroxide → 5-chloro-2-methylbenzotrifluoride

HRID 2399610Notes

Reaction equation

HRID 2399610 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:4]=1[CH:5](Cl)Cl.[OH-].[Na+].[H][H]>[Pd].[C].O>[CH3:5][C:4]1[CH:8]=[CH:9][C:10]([Cl:12])=[CH:11][C:3]=1[C:2]([F:13])([F:1])[F:14]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 10890716HCID 10890716, compound2×HCID 178418361HCID 178418361, compound2×

Product 1

HCID 117901015-chloro-2-methylbenzotrifluorideYield 122.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

A 1000-ml autoclave which is equipped with a mechanical stirrer and made of stainless steel (SUS-316) was charged with 263.6 g (1.0 mol) of the isomeric mixture (the product of the first step) containing 0.72 mol of 2-trifluoromethyl-4-chlorobenzalchloride as a main component, 84 g (2.1 mol) of sodium hydroxide and 420 g of water. Then, 5.3 g (2.0 wt %) of a metal-carried catalyst (5%-Pd/carbon) was added to the autoclave. The atmosphere of the autoclave was replaced by hydrogen, and the autoclave was put into oil bath to increase the temperature to 30° C. At the same time, stir was started while the hydrogen pressure was maintained at 5 kg/cm2. This started absorption of hydrogen. After the lapse of 4 hr, stir was stopped, and the reaction liquid was allowed to cool down. By analysis, conversion of 2-trifluoromethyl-4-chlorobenzalchloride (purity: 72.1%) was 99.9%. Then, the catalyst and the salt were removed by vacuum filtration. The resultant solution was put into a 1000-ml separating funnel, and then the aqueous phase was removed. The organic phase was washed with 500 ml of water and dried with magnesium sulfate. Then, magnesium sulfate was removed by vacuum filtration. As the result, 171.6 g of 2-methyl-5-chlorobenzotrifluoride (purity: 63.8%) was obtained. The yield of this product was 79.0%.

Workup

  1. customA 1000-ml autoclave which is equipped with a mechanical stirrer
  2. customthe autoclave was put into oil bath
  3. temperaturewas maintained at 5 kg/cm2
  4. customThis started absorption of hydrogen
  5. stirringAfter the lapse of 4 hr, stir
  6. customthe reaction liquid
  7. temperatureto cool down
  8. customThen, the catalyst and the salt were removed by vacuum filtration
  9. customseparating funnel
  10. customthe aqueous phase was removed
  11. washThe organic phase was washed with 500 ml of water
  12. dry with materialdried with magnesium sulfate
  13. customThen, magnesium sulfate was removed by vacuum filtration

Sources & evidence

ORD record
ord-ed4f692c12764861bbb7249f9f09f446
Source dataset
uspto-grants-1995_09
Patent number
US05449831

Reaction notes

Loading…