Sodium Hydroxide → 9-Octadecyn-1-ol

HRID 2371600Notes

Reaction equation

HRID 2371600 reaction equation
[CH2:1]([OH:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].BrBr.[OH-].[Na+]>>[CH2:1]([OH:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]#[C:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24408Bromine2×HCID 5284499Oleyl Alcohol

Product 1

HCID 117475479-Octadecyn-1-olYield 81.1%

Conditions

Temperature
15 °C

Procedure

Oleyl alcohol (9.80 g, 36.5 mmoles, Sigma) was placed in a 25 ml 3-neck roundbottom flask equipped with a thermometer, an overhead mechanical stirrer, and a reflux condenser. The contents of the flask were cooled to 15° C. and bromine (5.83 g, 36.5 mmole) was added slowly with stirring at such a rate as to keep the reaction temperature below 30° C. After addition of the bromine, the reaction was stirred at room temperature for 10 minutes. Polyethylene glycol 300 (1.0 g, Fluka) was added followed by powdered sodium hydroxide (3.65 g, 91.3 mmoles). A large exotherm was noted which brought the reaction temperature to 150° C. The reaction was stirred vigorously with heating to maintain a temperature of 125° C. for 2.5 hours. The reaction was cooled and filtered to remove the solid sodium bromide. The filtered salts were washed with 25 ml of hexanes and the solvent removed. The crude product was kugelrohr distilled (ca. 200° C./ 0.20 torr) to yield 9-octadecyn-l-ol (7.89 g, 81% yield) as a clear colorless liquid which solidified upon standing. 1H NMR (CDCl3): 3.61 (q, 2H), 2.12 (m, 4H), 1.02-1.87 (m, 25H), 0.88 (t, 3H) 13C NMR(CDCl3): 79.94, 79.84, 62.33, 32.48, 31.65, 29.19, 29.04, 28.96, 28.66, 28.61, 25.58, 22.45, 18.52, 13.84.

Workup

  1. customequipped with a thermometer, an overhead mechanical stirrer, and a reflux condenser
  2. customthe reaction temperature below 30° C
  3. stirringthe reaction was stirred at room temperature for 10 minutes
  4. customto 150° C
  5. stirringThe reaction was stirred vigorously
  6. temperaturewith heating
  7. temperatureto maintain a temperature of 125° C. for 2.5 hours
  8. temperatureThe reaction was cooled
  9. filtrationfiltered
  10. customto remove the solid sodium bromide
  11. washThe filtered salts were washed with 25 ml of hexanes
  12. customthe solvent removed
  13. distillationThe crude product was kugelrohr distilled (ca. 200° C./ 0.20 torr)

Sources & evidence

ORD record
ord-edeb8e0e17ad45589aa118f150e3368e
Source dataset
uspto-grants-1992_03
Patent number
US05093536

Reaction notes

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