2-Bromododecanoic acid → 2-chlorododecanoic Acid

HRID 1780686

Reaction equation

HRID 1780686 reaction equation
Br[CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:3]([OH:5])=[O:4].[Cl-:16].[Ca+2].[Cl-]>C(#N)C.[Cl-].C([N+](CC)(CC)CC)C>[Cl:16][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:3]([OH:5])=[O:4]

Participants

5

Reactant 2

HCID 669802-Bromododecanoic acidHCID 5284359Calcium Chloride

Product 1

HCID 43873702-chlorododecanoic Acid

Reagents, catalysts & solvents 2

HCID 5946Tetraethylammonium ChlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

To 2-bromododecanoic acid (1 g), after having been dissolved in acetonitrile (50 ml), were added calcium chloride (2 g) and tetraethylammonium chloride (1 g), and the mixture was heated under reflux for 4 hours. The reaction mixture was filtered, concentrated and distributed into ethyl acetate and water, and the ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated to give 2-chlorododecanoic acid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated
  5. dry with materialthe ethyl acetate layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4d66a7dbe24942be852784d3284035db
Source dataset
uspto-grants-1997_05
Patent number
US05631238

Linked notes

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