1-Octanol → Octanal

HRID 1272588Notes

Reaction equation

HRID 1272588 reaction equation
[CH2:1]([OH:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(=O)([O-])O.[Na+].[Br-].[Na+].C1C(=O)N(Cl)C(=O)C1>CC1(C)N([O])C(C)(C)CC(OC)C1.ClCCCl>[CH:1](=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 4

HCID 9571-OctanolHCID 31398ChlorosuccinimideHCID 253881Sodium BromideHCID 516892Sodium Bicarbonate

Product 1

HCID 454OctanalYield 85%

Reagents, catalysts & solvents 2

HCID 103134354-methoxy-TEMPOCatalystHCID 111,2-DichloroethaneSolvent

Procedure

1-Octanol (2.0 g, 15.4 mmol), sodium hydrogencarbonate (1.6 g, 18.5 mmol), 4-methoxy TEMPO (29 mg, 0.15 mmol), sodium bromide (0.16 g, 1.54 mmol) and 1,2-dichloroethane (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 NCS (2.3 g, 16.9 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 (1.67 g, yield 85%).

Workup

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

Sources & evidence

ORD record
ord-85fe6de52416405ea5fd4e9ef32b4093
Source dataset
uspto-grants-2007_04
Patent number
US07208634B2

Reaction notes

Loading…