Hydrochloric Acid → 3-(Trifluoromethoxy)benzaldehyde

HRID 26241Notes

Reaction equation

HRID 26241 reaction equation
Cl.[F:2][C:3]([F:14])([F:13])[O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[C:8]#N.C([O:17]CC)C>>[F:2][C:3]([F:14])([F:13])[O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH:8]=[O:17]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 1429623-(Trifluoromethoxy)benzonitrile

Product 1

HCID 6051393-(Trifluoromethoxy)benzaldehydeYield 44%

Conditions

Temperature
100 °C

Procedure

103 g (0.544 mol) of stannous chloride and 400 ml of diethyl ether are introduced into a one liter three-necked flask equipped with a condenser, a mechanical stirrer and a gas bubbler tube. This mixture is cooled and saturated with hydrogen chloride gas until the stannous chloride is completely dissolved. A solution of 72.7 g (0.388 mol) of 3-trifluoromethoxy-benzonitrile in 75 ml of anhydrous diethyl ether is added dropwise but fastly via the dropping funnel, while the mixture is cooled with ice-water. The mixture is allowed overnight, then the aldehyde is steam distilled. The distillate is extracted several times with diethyl ether and the extracts are combined. 250 ml of a solution of sodium bisulphite (d=1.32-1.33) are added to the extracts and allowed overnight. The bisulfite compound is filtered off, washed with a small quantity of ice-water and then with diethyl ether. The compound is introduced into a one liter flask which contains solution of 60 g of potassium carbonate in 250 ml of water. The mixture is heated at 100° C. so as to decompose the bisulfite compound and to steam distil the aldehyde as it is formed. The distillate is extracted several times with diethyl ether. The combined ether phases are dried over sodium sulphate and filtered and the solvent is evaporated. 32 g (44% yield) of 3-trifluoromethoxy-benzaldehyde are obtained as a colourless oil.

Workup

  1. customequipped with a condenser, a mechanical stirrer and a gas bubbler tube
  2. dissolutionis completely dissolved
  3. distillationdistilled
  4. extractionThe distillate is extracted several times with diethyl ether
  5. addition250 ml of a solution of sodium bisulphite (d=1.32-1.33) are added to the extracts
  6. waitallowed overnight
  7. filtrationThe bisulfite compound is filtered off
  8. washwashed with a small quantity of ice-water
  9. additionThe compound is introduced into a one liter flask which
  10. customto steam distil the aldehyde as it
  11. customis formed
  12. extractionThe distillate is extracted several times with diethyl ether
  13. dry with materialThe combined ether phases are dried over sodium sulphate
  14. filtrationfiltered
  15. customthe solvent is evaporated

Sources & evidence

ORD record
ord-4404e86780b947c69022bde0680dd9ba
Source dataset
uspto-grants-1979_04
Patent number
US04148923

Reaction notes

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