1-Octanol → Octyl bromoacetate

HRID 1517508Notes

Reaction equation

HRID 1517508 reaction equation
C(=O)([O-])[O-].[K+].[K+].O1CCOCC1.[Br:13][CH2:14][C:15](Br)=[O:16].[CH2:18]([OH:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>>[Br:13][CH2:14][C:15]([O:26][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[O:16]

Participants

5

Reactant 4

HCID 9571-OctanolHCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 61147Bromoacetyl bromide

Product 1

HCID 347413Octyl bromoacetate

Procedure

Finely ground potassium carbonate (41.1 g) is added to a stirred dioxane solution of Octyl alcohol (36.9 g) cooled by an ice bath followed by addition over approximately 15 minutes of 2-bromoacetyl bromide (40.0 g). The mixture is stirred overnight, filtered and the dioxane is removed under vacuum. The residue is taken up in dichloromethane, washed with 10% HCl, water, sodium bicarbonate, and dried over magnesium sulfate. After removal of the solvent, the product is obtained as a light yellow oil.

Workup

  1. temperaturecooled by an ice bath
  2. filtrationfiltered
  3. customthe dioxane is removed under vacuum
  4. washwashed with 10% HCl, water, sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. customAfter removal of the solvent
  7. customthe product is obtained as a light yellow oil

Sources & evidence

ORD record
ord-51dd60c623cd4a13b491b0e13a427b79
Source dataset
uspto-grants-2012_07
Patent number
US08232305B2

Reaction notes

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