Formic Acid → 4-(Trifluoromethyl)benzaldehyde

HRID 893422Notes

Reaction equation

HRID 893422 reaction equation
N#N.[F:3][C:4]([F:14])([F:13])[C:5]1[CH:12]=[CH:11][C:8]([C:9]#N)=[CH:7][CH:6]=1.C(O)=[O:16]>[Ni].[Al]>[F:3][C:4]([F:14])([F:13])[C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:16])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 947NitrogenHCID 67995Benzonitrile, 4-(trifluoromethyl)-

Product 1

HCID 679964-(Trifluoromethyl)benzaldehydeYield 87.9%

Reagents, catalysts & solvents 1

HCID 6336846Nickel aluminideCatalyst

Conditions

Temperature
80 °C

Procedure

A Parr hydrogenation bottle was purges with N2 and then charged with 25 g of 4-trifluoromethyl benzonitrile, 250 mL of 75% aqueous formic acid and 3.0 g of powdered nickel/aluminum alloy catalyst (50/50). The reaction mixture was shaken at 80° C. with H2 gas (3 atmospheres pressure) for 16 hours. The reaction mixture was continuously extracted with CH2Cl2 and analyzed via Internal Standard GLC which indicated 87.9% yield of 4-trifluoromethyl benzaldehyde.

Workup

  1. extractionThe reaction mixture was continuously extracted with CH2Cl2

Sources & evidence

ORD record
ord-f35ba17213594fcaac09011213d04e75
Source dataset
uspto-grants-1992_06
Patent number
US05124487

Reaction notes

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