Sodium Hydroxide → HCID 19907834, compound

HRID 2371601Notes

Reaction equation

HRID 2371601 reaction equation
[CH2:1]([OH:19])[CH2:2][CH2:3][CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8][CH2:9][CH2:10][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][C:6]#[C:7][CH2:8][CH2:9][CH2:10][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 9856654(6Z)-6-Octadecen-1-ol

Product 1

HCID 19907834HCID 19907834, compoundYield 75%

Conditions

Temperature
125 °C

Procedure

Petroselinyl alcohol (0.66 g, 2.46 mmoles, Sigma) was placed in a 10 ml 3-neck roundbottom flask equipped with a reflux condenser. Bromine (0.40 g, 2.5 mmole) was added slowly with magnetic stirring. After addition of the bromine, polyethylene glycol 300 (60 mg, Fluka) was added followed by powdered sodium hydroxide (0.250 g, 6.25 mmoles). A large exotherm was noted. 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 6-octadecyn-1-ol (0.49 g, 75% yield) as a clear colorless liquid which solidified upon standing.

Workup

  1. customequipped with a reflux condenser
  2. additionwas added
  3. temperaturewith heating
  4. temperatureThe reaction was cooled
  5. filtrationfiltered
  6. customto remove the solid sodium bromide
  7. washThe filtered salts were washed with 25 ml of hexanes
  8. customthe solvent removed
  9. distillationThe crude product was kugelrohr distilled (ca. 200° C./ 0.20 torr)

Sources & evidence

ORD record
ord-abe40159e0df4c2c92130eb86352b8a7
Source dataset
uspto-grants-1992_03
Patent number
US05093536

Reaction notes

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