Formic Acid → 4-Chloro-2-(trifluoromethyl)benzaldehyde

HRID 252135Notes

Reaction equation

HRID 252135 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#N)=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1.C(O)=[O:15].O>C(OCC)(=O)C.[Al].[Ni]>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:15])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1

Participants

6

Reactant 3

HCID 284Formic AcidHCID 962WaterHCID 27734954-Chloro-2-(trifluoromethyl)benzonitrile

Product 1

HCID 27790174-Chloro-2-(trifluoromethyl)benzaldehydeYield 87%

Reagents, catalysts & solvents 2

HCID 6336846Nickel aluminideCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Add 4-chloro-2-trifluoromethyl-benzonitrile to formic acid (96%) (15 mL) and water (3 mL). Add nickel-aluminum alloy (1260 mg). Heat at 100° C. overnight. Dilute with ethyl acetate and filter through Celite®. Extract the filtrate with 1 N sodium hydroxide and saturated aqueous sodium chloride, dry (sodium sulfate), filter, and concentrate to give 4-chloro-2-trifluoromethylbenzaldehyde (555 mg, 87%): 1H NMR (400 MHz, MeOH-d4) δ 10.29 (m, 1H), 8.10 (d, 1H, J=8.4 Hz), 7.91 (d, 1H, J=1.6 Hz), 7.85 (dd, 1H, J=8.4, 1.6 Hz).

Workup

  1. filtrationfilter through Celite®
  2. extractionExtract the filtrate with 1 N sodium hydroxide and saturated aqueous sodium chloride
  3. dry with materialdry (sodium sulfate)
  4. filtrationfilter
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-d0908532718b44929471bf42459ef1dd
Source dataset
uspto-grants-2011_01
Patent number
US07868014B2

Reaction notes

Loading…