Formic Acid → 2,4,6-Trichlorobenzaldehyde

HRID 252145Notes

Reaction equation

HRID 252145 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([Cl:11])[C:3]=1[C:4]#N.C(O)=[O:13].O.[Al]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([Cl:11])[C:3]=1[CH:4]=[O:13]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 962WaterHCID 5221792,4,6-TrichlorobenzonitrileHCID 5359268Aluminum

Product 1

HCID 53144572,4,6-TrichlorobenzaldehydeYield 93%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Add 2,4,6-trichlorobenzonitrile (206 mg, 1.0 mmol) to 96% formic acid (5 mL, 96%) and water (1 mL). Add nichol/aluminum alloy (206 mg) to the mixture. Heat at 100° C. for 4 hours. 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 2,4,6-trichlorobenzaldehyde (195 mg, 93%). 1H NMR (400 MHz, CDCl3) δ 10.36 (s, 1H), 7.99 (s, 1H), 7.61 (s, 1H).

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-4c9c25f344e344478903b42e7d30873b
Source dataset
uspto-grants-2011_01
Patent number
US07868014B2

Reaction notes

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