1-Bromooctadecane → 2-Heneicosanone

HRID 1435100Notes

Reaction equation

HRID 1435100 reaction equation
[CH3:1][C:2](=O)[CH2:3][C:4](=[O:6])[CH3:5].Br[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]CC.C1OCCOCCOCCOCCOCCOC1.C(=O)([O-])[O-].[K+].[K+]>O.C(O)C>[CH3:5][C:4](=[O:6])[CH2:3][CH2:2][CH2:1][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH3:9]

Participants

7

Reactant 4

HCID 82181-BromooctadecaneHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 31261Acetylacetone

Product 1

HCID 5298052-HeneicosanoneYield 95%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a 2 L two-necked round bottom flask equipped with water condenser, calcium chloride guard tube and mechanical stirrer, 70 g of 2,4-pentanedione, 650 g of 1-bromooctadecane, 8 g of 18-crown-6, anhydrous potassium carbonate 140 g and 600 ml of absolute ethanol were added with stirring. The mixture was refluxed at 90° C. with continuous stirring for 30 hrs; after refluxing at the said temperature, the mixture cooled to ambient temperature (25° C.), 600 ml of water was added to it and the 2-heneicosanone was extracted with dichloromethane from the mixture. On distillation of dichloromethane, 2-heneicosanone was obtained.

Workup

  1. customTo a 2 L two-necked round bottom flask equipped with water condenser, calcium chloride guard tube and mechanical stirrer
  2. stirringwith continuous stirring for 30 hrs
  3. temperatureafter refluxing at the said temperature
  4. additionwas added to it
  5. extractionthe 2-heneicosanone was extracted with dichloromethane from the mixture
  6. distillationOn distillation of dichloromethane

Sources & evidence

ORD record
ord-34db3af5ede04e69a68440116697d694
Source dataset
uspto-grants-2009_11
Patent number
US07615672B2

Reaction notes

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