1-Octanol → Octanal

HRID 1272587Notes

Reaction equation

HRID 1272587 reaction equation
[CH2:1]([OH:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C([O-])(=O)C.[Na+]>CC1(C)N(O)C(C)(C)CC(O)C1.ClCCl>[CH:1](=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 2

HCID 9571-OctanolHCID 517045Sodium Acetate

Product 1

HCID 454OctanalYield 90.2%

Reagents, catalysts & solvents 2

HCID 53951,4-Dihydroxy-2,2,6,6-tetramethylpiperidineCatalystHCID 6344DichloromethaneSolvent

Procedure

1-Octanol (2.0 g, 15.4 mmol), sodium acetate (1.8 g, 21.6 mmol), 4-hydroxy TEMPO (53 mg, 0.31 mmol) and dichloromethane (15 ml) were put in a 50-ml egg plant type flask. The suspension was cooled to less than 10° C. in an ice bath, and thereto was added NBA (2.5 g, 18.5 mmol)divided in two portions. The insoluble materials were filtered off and the filtrate was washed with 5% aqueous sodium bicarbonate solution. The crude product was purified by distillation to give 1-octanal (1.78 g, yield 90%).

Workup

  1. temperatureThe suspension was cooled to less than 10° C. in an ice bath
  2. additionwas added NBA (2.5 g, 18.5 mmol)
  3. filtrationThe insoluble materials were filtered off
  4. washthe filtrate was washed with 5% aqueous sodium bicarbonate solution
  5. distillationThe crude product was purified by distillation

Sources & evidence

ORD record
ord-96d36257b602482884aaf25c97280d90
Source dataset
uspto-grants-2007_04
Patent number
US07208634B2

Reaction notes

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