Allyl bromide → HCID 86642022, compound

HRID 414894Notes

Reaction equation

HRID 414894 reaction equation
[H-].[Na+].[CH3:3][C:4]([OH:13])([CH2:7][CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])[CH2:5][CH3:6].[CH2:14](Br)[CH:15]=[CH2:16]>CN(C)C=O>[CH2:16]([O:13][C:4]([CH3:3])([CH2:5][CH3:6])[CH2:7][CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])[CH:15]=[CH2:14]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 867493,7-Dimethyloct-6-en-3-ol

Product 1

HCID 86642022HCID 86642022, compoundYield 786.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil, 6.8 g, 170 mmol) and dimethylformamide (100 mL) were added to a three necked 500 mL flask fitted with thermocouple, condenser and addition funnel. To the stirred reaction mixture was added dropwise 3,7-dimethyloct-6-en-3-ol (22 g, 139 mmol) at room temperature. The mixture was stirred for 1 hr, cooled to ice bath temperature then allyl bromide (97% pure by GC RPA, 19 g, 15 mmol) was added dropwise whilst maintaining cooling. After a further 3 hr stirring ice/water was added to the reaction mixture and then extracted with methyltert-butyl ether (3×30 mL). The combined organic phase was washed with dilute hydrochloric acid (100 mL), saturated brine (100 mL) and dried with magnesium sulphate. The solvent was removed in vacuo and the residue fractionally distilled to give 6-(allyloxy)-2,6-dimethyloct-2-ene (25.4 g, 92% pure by GC RPA, 118 mmol, chemical yield 70%).

Workup

  1. customfitted with thermocouple, condenser and addition funnel
  2. customTo the stirred reaction mixture
  3. temperaturecooled to ice bath temperature
  4. temperaturewhilst maintaining
  5. temperaturecooling
  6. additionwas added to the reaction mixture
  7. extractionextracted with methyltert-butyl ether (3×30 mL)
  8. washThe combined organic phase was washed with dilute hydrochloric acid (100 mL), saturated brine (100 mL)
  9. dry with materialdried with magnesium sulphate
  10. customThe solvent was removed in vacuo
  11. distillationthe residue fractionally distilled

Sources & evidence

ORD record
ord-0aefe937aefc48c5a03fe6afe022e6a1
Source dataset
uspto-grants-2012_01
Patent number
US08088725B2

Reaction notes

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