Ammonia → 7-(4-Octylphenyl)hept-5-YN-1-OL

HRID 1995776Notes

Reaction equation

HRID 1995776 reaction equation
[NH2-].[Li+].N.[Li].Br[CH2:6][CH2:7][CH2:8][CH2:9][OH:10].[CH2:11]([C:19]1[CH:27]=[CH:26][C:22]([CH2:23][C:24]#[CH:25])=[CH:21][CH:20]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>>[CH2:11]([C:19]1[CH:20]=[CH:21][C:22]([CH2:23][C:24]#[C:25][CH2:6][CH2:7][CH2:8][CH2:9][OH:10])=[CH:26][CH:27]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 5

HCID 222Ammonia3×HCID 24532Lithium amideHCID 1183884-BromobutanolHCID 3028194LithiumHCID 204880011-Octyl-4-(prop-2-YN-1-YL)benzene

Product 1

HCID 204880187-(4-Octylphenyl)hept-5-YN-1-OL

Procedure

A solution of lithium amide in liquid ammonia is prepared by the addition of lithium metal (2 mmoles) to liquid ammonia containing a trace amount of ferrous sulfate. To this solution is added 4-bromo-n-butanol (1 mmole) and p-(n-octyl)benzylacetylene (1 mmole, prepared as described in paragraph B of Example 6 or in paragraph A of this example). After a suitable time at refluxing liquid ammonia temperatures, the ammonia is removed by evaporation and the residue dissolved in water. After extraction with chloroform, the chloroform layer is separated and the solvent removed by evaporation to give a residue. This residue is purified by distillation under vacuum to give 7-[p-(n-octyl)phenyl]-5-heptyn-1-ol.

Workup

  1. customprepared
  2. customthe ammonia is removed by evaporation
  3. dissolutionthe residue dissolved in water
  4. extractionAfter extraction with chloroform
  5. customthe chloroform layer is separated
  6. customthe solvent removed by evaporation
  7. customto give a residue
  8. distillationThis residue is purified by distillation under vacuum

Sources & evidence

ORD record
ord-5ef856cfc40e4bf39154dcfc7e6cff9a
Source dataset
uspto-grants-1983_09
Patent number
US04405810

Reaction notes

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