4-(Trifluoromethyl)benzoyl chloride → 4-(Trifluoromethyl)benzaldehyde

HRID 904794Notes

Reaction equation

HRID 904794 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.[H][H].[C]=O>C1(C)C=CC=CC=1.[Pd].[C]>[F:1][C:2]([F:12])([F:13])[C:3]1[CH:11]=[CH:10][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 178418361HCID 178418361, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 679964-(Trifluoromethyl)benzaldehydeYield 83%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalyst2×HCID 1140TolueneSolvent2×

Procedure

In an apparatus as in Example 2, 100 g of 4-trifluoromethylbenzoyl chloride which had been prepared analogously to Example 1 were hydrogenated in the course of 4 hours at 90° C. in 700 ml of dry toluene with the aid of 3.5 g of Pd-carbon (Pd content: 5% by weight); the conversion was 95%. The Pd-carbon catalyst had been exposed, before the hydrogenation, for 30 minutes in toluene at the boil to a mixture containing 50% by volume each of hydrogen and carbon monoxide. By distillation it was possible to obtain 69.2 g of 4-trifluoromethylbenzaldehyde which had a boiling point of 70°-71° C./20 mbars and an nD20 of 1.4639. Yield: 83% of theory.

Workup

  1. distillationBy distillation it

Sources & evidence

ORD record
ord-97914393e7794d0a9de5102e56574059
Source dataset
uspto-grants-1983_12
Patent number
US04420433

Reaction notes

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