Hydrochloric Acid → 3-(Trifluoromethyl)benzaldehyde

HRID 904792Notes

Reaction equation

HRID 904792 reaction equation
S1(CCCC1)(=O)=O.[F:8][C:9]([F:20])([F:19])[C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13](Cl)=[O:14].[H][H].Cl>[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[F:8][C:9]([F:19])([F:20])[C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[CH:13]=[O:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 31347SulfolaneHCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 679903-(Trifluoromethyl)benzaldehydeYield 84%

Reagents, catalysts & solvents 1

HCID 16218511Pd barium sulfateCatalyst

Procedure

In a three-necked flask equipped with a stirrer, a gas inlet tube and a reflux condenser, 250 g of sulpholane (thiolane-S-dioxide), 5 g of Pd-BaSO4 (Pd content: 5% by weight) and 100 g (0.48 mol) of 3-trifluoromethylbenzoyl chloride from Example 1 are heated at 140° C. while hydrogen is being passed through. The elimination of hydrogen chloride which commenced immediately was complete in 3 hours. The 3-trifluoromethylbenzaldehyde formed was distilled off without the catalyst having been filtered off. Boiling point 69°-70° C./20 mbars, nD20 1.4648, 70 g; Yield: 84% of theory.

Workup

  1. customIn a three-necked flask equipped with a stirrer, a gas inlet tube and a reflux condenser

Sources & evidence

ORD record
ord-05ebb4a87ac542d8ad3bd65a7d6ce868
Source dataset
uspto-grants-1983_12
Patent number
US04420433

Reaction notes

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