1-Piperidinecarboxaldehyde → 5-Chloro-2-methylbenzaldehyde

HRID 1066361Notes

Reaction equation

HRID 1066361 reaction equation
Br[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH3:9].[Li]CCCC.[CH:15](N1CCCCC1)=[O:16]>C1COCC1>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([CH3:9])=[C:2]([CH:7]=1)[CH:15]=[O:16]

Participants

5

Reactant 3

HCID 174291-PiperidinecarboxaldehydeHCID 6098982-Bromo-4-chloro-1-methylbenzeneHCID 178418339Butyllithium

Product 1

HCID 123475655-Chloro-2-methylbenzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-bromo-4-chlorotoluene (20.0 g; 97.3 mmol) in 300 mL of THF at −78° C. was added dropwise a 2.5 M solution of n-BuLi (102.2 mmol). After 30 min of stirring at that temperature, 1-formylpiperidine (11.4 mL) in 10 mL of THF was added and the solution left for 1 h. It was brought to 0° C. , quenched with NH4OAc (25%) and diluted with EtOAc. The organic phase was dried over Na2SO4, filtered and the solvent removed to yield 13.3 g of the title compound.

Workup

  1. additionwas added
  2. customwas brought to 0° C.
  3. customquenched with NH4OAc (25%)
  4. additiondiluted with EtOAc
  5. dry with materialThe organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent removed

Sources & evidence

ORD record
ord-3d03072eea70413b9486bc532f688958
Source dataset
uspto-grants-2001_06
Patent number
US06242493B1

Reaction notes

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