1-Octanol → HCID 12642364, compound

HRID 1384409Notes

Reaction equation

HRID 1384409 reaction equation
[H-].[Na+].[CH2:3]([OH:11])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].Br[CH2:13][C:14]#[N:15]>COCCOC>[CH2:3]([O:11][CH2:13][C:14]#[N:15])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 9571-OctanolHCID 11534BromoacetonitrileHCID 24758Sodium hydride

Product 1

HCID 12642364HCID 12642364, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a suspension of 15.60 g sodium hydride (60%) in 200 ml of 1,2-dimethoxyethane, 50.79 g of 1-octanol was dropped in. The mixture was stirred for 45 minutes at room temperature. Then, 46.76 g of bromoacetonitrile was dropped in. The reaction mixture was refluxed for 2 hours, quenched with water, filtered, and diluted with brine. After extraction with ether, the organic layer was washed with brine and water, dried, filtered, and evaporated to dryness. The resulting dark oil was purified by distillation to yield a yellow oil.

Workup

  1. additionwas dropped in
  2. temperatureThe reaction mixture was refluxed for 2 hours
  3. customquenched with water
  4. filtrationfiltered
  5. additiondiluted with brine
  6. extractionAfter extraction with ether
  7. washthe organic layer was washed with brine and water
  8. customdried
  9. filtrationfiltered
  10. customevaporated to dryness
  11. distillationThe resulting dark oil was purified by distillation
  12. customto yield a yellow oil

Sources & evidence

ORD record
ord-b31b1c99fe1341fea777bcf19b67ed90
Source dataset
uspto-grants-2001_07
Patent number
US06258854B1

Reaction notes

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