Hexane → HCID 12728680, compound

HRID 840073Notes

Reaction equation

HRID 840073 reaction equation
CCCCCC.[OH-].[Na+].[CH2:9]([OH:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[Br:16][C:17]([CH2:19]Br)=[CH2:18]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Br:16][C:17]([CH2:19][O:15][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH2:18]

Participants

7

Reactant 4

HCID 8058HexaneHCID 81031-HexanolHCID 105522,3-DibromopropeneHCID 14798Sodium Hydroxide

Product 1

HCID 12728680HCID 12728680, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

To a three neck round bottom flask equipped with an addition funnel and an overhead stirrer was added 35 ml of hexane, 42 g of 50% sodium hydroxide and 0.50 g of tetra-n-butylammonium bromide. A mixture of 6.74 g of hexanol (66 mmol) and 20 g (100 mmol) of 2,3-dibromopropene were fed to the well-stirred reaction mixture over a 20 minute period. The reaction was stirred an additional 1 hour, then water was added, and the phases were separated. The organic phase was washed with water and brine, dried over magnesium sulfate, filtered and stripped. The product was fractionally distilled under reduced pressure to give 6.1 g of 95% pure 2-bromo-3-hexyloxypropene.

Workup

  1. customTo a three neck round bottom flask equipped with an addition funnel and an overhead stirrer
  2. customwere fed to the well-stirred reaction mixture over a 20 minute period
  3. customthe phases were separated
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. distillationThe product was fractionally distilled under reduced pressure

Sources & evidence

ORD record
ord-563397aa91c04bb2a6ddbf7fb67ad896
Source dataset
uspto-grants-2002_04
Patent number
US06365549B2

Reaction notes

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