HCID 53679904, compound → 3-Trifluoromethylthio-benzaldehyde

HRID 26238Notes

Reaction equation

HRID 26238 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[S:7].[H][H]>C1(C)C=CC=CC=1.[Pd]>[F:1][C:2]([F:12])([F:13])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[CH:6]=[S:7]

Participants

5

Reactant 2

HCID 53679904HCID 53679904, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 545219343-Trifluoromethylthio-benzaldehydeYield 73.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

A solution of 56.9 g (237 mmols) of 3-trifluoromethyl-thiobenzoic acid chloride in 285 ml of anhydrous toluene and 5.7 g of 5 percent strength palladium on barium sulphate is introduced into a one liter three-necked flask equipped with a condenser, a mechanical stirrer and a gas bubbler tube. This mixture is heated, with stirring, for 12 hours at the reflex temperature, while a gentle stream of hydrogen is bubbled through it. The catalyst is filtered off and washed with diethyl ether. 125 ml of a solution of sodium bisulphite (d=1.33) are added to the filtrate. This mixture is stirred vigorously for 24 hours and the bisulphite compound is filtered off, washed with diethyl ether and introduced into a three-necked flask. A solution of 80 g of potassium carbonate in 500 ml of water is added and the mixture is boiled, so as to steam distil the aldehyde as it is formed. The distillate is extracted twice in succession with diethyl ether. The combined ether phases are dried over sodium sulphate and filtered. The solvent is evaporated in vacuo on a water bath and the residue is rectified. 33.3 g (67% yield) of 3-trifluoromethylthio-benzaldehyde, as an oil, b.p. 108°-111° C./30-38 mm.Hg, are thus obtained.

Workup

  1. customequipped with a condenser, a mechanical stirrer and a gas bubbler tube
  2. temperatureThis mixture is heated
  3. customis bubbled through it
  4. filtrationThe catalyst is filtered off
  5. washwashed with diethyl ether
  6. addition125 ml of a solution of sodium bisulphite (d=1.33) are added to the filtrate
  7. filtrationthe bisulphite compound is filtered off
  8. washwashed with diethyl ether
  9. additionintroduced into a three-necked flask
  10. additionA solution of 80 g of potassium carbonate in 500 ml of water is added
  11. customdistil the aldehyde as it
  12. customis formed
  13. extractionThe distillate is extracted twice in succession with diethyl ether
  14. dry with materialThe combined ether phases are dried over sodium sulphate
  15. filtrationfiltered
  16. customThe solvent is evaporated in vacuo on a water bath

Sources & evidence

ORD record
ord-11163367d38942489bc1184cd97787fe
Source dataset
uspto-grants-1979_04
Patent number
US04148923

Reaction notes

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