Formic Acid → 3-Chloro-4-methylbenzaldehyde

HRID 638613Notes

Reaction equation

HRID 638613 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH3:10])[C:5]#N.C(O)=[O:12]>[Al].[Ni]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH3:10])[CH:5]=[O:12]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 888943-Chloro-p-toluonitrile

Product 1

HCID 124230853-Chloro-4-methylbenzaldehyde

Reagents, catalysts & solvents 1

HCID 6336846Nickel aluminideCatalyst

Procedure

A mixture of 3-chloro-4-methylbenzonitrile (4.0 g, 26.39 mmol), formic acid (72 ml, 75% v/v) and nickel aluminum alloy (50/50, 4.8 g) was stirred and heated under reflux for 2 h. The reaction mixture was then filtered hot through Hyflo, and the residue was washed well with hot ethanol. The filtrate was concentrated under reduced pressure to yield a sticky solid. Distillation of this solid afforded 3-chloro-4-methylbenzaldehyde as a colourless oil, b.p. 73°-74°/0.8 mmHg.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 h
  3. filtrationThe reaction mixture was then filtered hot through Hyflo
  4. washthe residue was washed well with hot ethanol
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customto yield a sticky solid
  7. distillationDistillation of this solid

Sources & evidence

ORD record
ord-07dc61c1194a4282bc32f8d2ac9f7791
Source dataset
uspto-grants-1985_12
Patent number
US04562199

Reaction notes

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