1-Octanol → HCID 53635237, compound

HRID 905097Notes

Reaction equation

HRID 905097 reaction equation
[H-].[Na+].[CH2:3]([OH:11])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[H][H].Br[CH2:15][C:16]1[CH:33]=[CH:32][C:19]([CH:20]=[C:21]2[CH:26]3[C:27]([CH3:29])([CH3:28])[C:23]([CH3:30])([CH2:24][CH2:25]3)[C:22]2=[O:31])=[CH:18][CH:17]=1>C1(C)C=CC=CC=1.O>[CH2:3]([O:11][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([CH:20]=[C:21]2[CH:26]3[C:27]([CH3:28])([CH3:29])[C:23]([CH3:30])([CH2:24][CH2:25]3)[C:22]2=[O:31])=[CH:32][CH:33]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

7

Reactant 4

HCID 9571-OctanolHCID 24758Sodium hydrideHCID 53777893HCID 53777893, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53635237HCID 53635237, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A suspension of 2.1 g (50 millimols) of sodium hydride (in oil) is added in small amounts to 6.5 g (50 millimols) of octan-1-ol in 100 ml of toluene, whilst stirring. When the evolution of hydrogen has ended, 16.6 g (50 millimols) of 3-(p-bromomethylbenzylidene)-camphor are added in portions, and the mixture is then heated under reflux for 3 hours. After adding water, the toluene phase is decanted, dried and concentrated to dryness. The residual syrup is distilled under reduced pressure. 8.8 g of a yellow liquid, which boils at 240° under a pressure of 0.1 mm Hg, are thus collected.

Workup

  1. temperaturethe mixture is then heated
  2. temperatureunder reflux for 3 hours
  3. customthe toluene phase is decanted
  4. customdried
  5. concentrationconcentrated to dryness
  6. distillationThe residual syrup is distilled under reduced pressure
  7. custom8.8 g of a yellow liquid, which boils at 240° under a pressure of 0.1 mm Hg, are thus collected

Sources & evidence

ORD record
ord-dc9011886d4a44bf80750b718a241b3f
Source dataset
uspto-grants-1983_12
Patent number
US04421739

Reaction notes

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