Sodium Azide → 10-Azidodecanoic acid

HRID 2280232Notes

Reaction equation

HRID 2280232 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12].[N-:14]=[N+:15]=[N-:16].[Na+]>CC(C)=O>[N:14]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[N+:15]=[N-:16]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 14271210-Bromodecanoic Acid

Product 1

HCID 8571414410-Azidodecanoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

10-Bromodecanoic acid (2.51 g, 10 mmol) in acetone (50 mL) is treated with sodium azide (0.75 g, 11 mmol) at reflux for 2 h. The reaction is then concentrated in vacuo to a gum that is partitioned between ethyl acetate (50 mL) and water (50 mL). The organic phase is separated, dried over sodium sulfate and concentrated in vacuo to give 10-azidodecanoic acid (2.02 g, 95%).

Workup

  1. temperatureat reflux for 2 h
  2. concentrationThe reaction is then concentrated in vacuo to a gum that
  3. customis partitioned between ethyl acetate (50 mL) and water (50 mL)
  4. customThe organic phase is separated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c8b692c415bc4f58a3b85e16c74c87f5
Source dataset
uspto-grants-2015_09
Patent number
US09138493B2

Reaction notes

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