1-Octanol → Octanal

HRID 399608Notes

Reaction equation

HRID 399608 reaction equation
ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O.C([O-])(=O)C.[Na+].[CH2:18]([OH:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>C(Cl)Cl.CC1(C)N([O])C(C)(C)CCC1>[CH:18](=[O:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 3

HCID 9571-OctanolHCID 6909Trichloroisocyanuric AcidHCID 517045Sodium Acetate

Product 1

HCID 454OctanalYield 91.4%

Reagents, catalysts & solvents 2

HCID 2724126TempoCatalystHCID 6344DichloromethaneSolvent2×

Procedure

3.5 g (15.1 mmol) of trichloroisocyanuric acid, 3.7 g (45.1 mmol) of sodium acetate and 10 mg (0.06 mmol) of TEMPO were suspended in 40 ml of methylene chloride in a 100 ml sulphonation flask and the suspension was cooled to (-7)-(-9)° C. while stirring. A solution of 5 g (38.4 mmol) of 1-octanol in 20 ml of methylene chloride was dosed in within 20 minutes, whereupon the mixture was held at (-7)-(-9)° C. for 80 minutes. Thereafter, the reaction had finished. For the working up, the white precipitate was filtered off and the filtrate was washed with sodium bicarbonate solution and with sodium chloride solution. Distillation of the crude product gave 4.5 g (91%) of octanal, GC content: (98.2%) (area percent).

Workup

  1. temperaturethe suspension was cooled to (-7)-(-9)° C
  2. customwas dosed in within 20 minutes, whereupon the mixture
  3. filtrationFor the working up, the white precipitate was filtered off
  4. washthe filtrate was washed with sodium bicarbonate solution and with sodium chloride solution
  5. distillationDistillation of the crude product

Sources & evidence

ORD record
ord-21573c3debe24a6484571cb035994f84
Source dataset
uspto-grants-1998_10
Patent number
US05821374

Reaction notes

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