Hydrochloric Acid → 3'-(Trifluoromethyl)acetophenone

HRID 634975Notes

Reaction equation

HRID 634975 reaction equation
Cl.N[C:3]1[CH:4]=[C:5]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:7][CH:8]=1.N([O-])=[O:14].[Na+].[CH:17](=NO)[CH3:18]>O.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH3:18][C:17]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]([F:12])([F:11])[F:10])[CH:4]=1)=[O:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 73753-(Trifluoromethyl)anilineHCID 7863AldoximeHCID 23668193Sodium Nitrite

Product 1

HCID 676823'-(Trifluoromethyl)acetophenoneYield 51.8%

Reagents, catalysts & solvents 2

HCID 61499Cupric sulfate monohydrateCatalystHCID 962WaterSolvent3×

Conditions

Temperature
-7.5 °C

Procedure

Under nitrogen, 1290 g of water and 740 g of hydrochloric acid (30% by weight strength) were initially charged and cooled to from −10 to −5° C. At below −5° C., 334 g of 3-aminobenzotrifluoride were then metered in (content 99.9%). 149 g of sodium nitrite were dissolved in 690 g of water and metered in at below 0° C. over the course of 2 hours. The mixture was then stirred for another 1 hour. Under nitrogen, an initial charge of 24 g of copper sulphate hydrate, 73 g of water and 183 g of acetaldoxime was heated to 28° C., and the diazonium salt solution which had been prepared beforehand was metered in with intensive stirring over the course of 2 hours. The mixture was allowed to react at 30° C. for another 30 minutes. After 1 hour, the mixture was heated to 100° C. and the crude product was distilled off together with water. After the removal of the water from the distillate, the crude product was distilled over a column. 202 g of 3-trifluoromethylacetophenone were obtained (content according to GC 99.1%). This corresponds to a yield of 51.5% of theory.

Workup

  1. customAt below −5° C.
  2. custommetered in at below 0° C. over the course of 2 hours
  3. temperaturewas heated to 28° C.
  4. stirringwith intensive stirring over the course of 2 hours
  5. customto react at 30° C. for another 30 minutes
  6. waitAfter 1 hour
  7. temperaturethe mixture was heated to 100° C.
  8. distillationthe crude product was distilled off together with water
  9. customAfter the removal of the water from the distillate
  10. distillationthe crude product was distilled over a column

Sources & evidence

ORD record
ord-856ebad90a3e4f7085e22062f983700b
Source dataset
uspto-grants-2001_02
Patent number
US06184417B2

Reaction notes

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