Lithium Hydroxide → 6-azidohexanoic Acid

HRID 1484202Notes

Reaction equation

HRID 1484202 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O:11]C)=[O:10])=[N+:2]=[N-:3].CO.O.[Li+].[OH-]>[Cl-].[Na+].O>[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 11446587HCID 11446587, compoundHCID 22242641Methanol--water (1/1)

Product 1

HCID 110409496-azidohexanoic AcidYield 93%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

AHA was synthesized following a reported method with modifications. To methyl 6-azidohexanoate (3.4 g, 20 mmol) in 20 ml of mixture of MeOH/H2O (4/1 v/v) LiOH (2.5 g, 60 mmol) was added. After being stirred for 5 h at room temperature, the reaction mixture was poured into brine and washed with hexane to remove unreacted Ester. The aqueous fraction was acidified with HCl, extracted with ethyl acetate. Combined organic fractions were washed with brine and died over MgSO4. Ethyl acetate was removed under reduced pressure that resulted to transparent liquid. Yield 93%.

Workup

  1. customAHA was synthesized
  2. washwashed with hexane
  3. customto remove unreacted Ester
  4. extractionextracted with ethyl acetate
  5. washCombined organic fractions were washed with brine
  6. customEthyl acetate was removed under reduced pressure that
  7. customresulted to transparent liquid

Sources & evidence

ORD record
ord-ee4ce61f19e14bda86fd99fe8a65fd29
Source dataset
uspto-grants-2016_08
Patent number
US09421276B2

Reaction notes

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