Acetic Acid → 11-Aminoundecanoic acid

HRID 1440349Notes

Reaction equation

HRID 1440349 reaction equation
COC([NH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=O.[OH-].[Na+].C(O)(=O)C>C(O)C.O.[Au]>[NH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 11032601HCID 11032601, compound

Product 1

HCID 1708311-Aminoundecanoic acidYield 34%

Reagents, catalysts & solvents 3

HCID 23985GoldCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

1.0 g (3.9×10-3 mol) of 11-(methoxycarbonylamino) undecanoic acid, is dissolved in 20 mL ethanol and added to 2.0 g (5.0×10-2 mol) sodium hydroxide in 2 mL water. The mixture is refluxed for 17 hours, and the resulting gold-colored solution is cooled and neutralized with acetic acid to a pH of 7. The neutralized solution is filtered to remove any salt and the filtrate is stripped to yield crude amino acid. The crude acid is dissolved in 50 mL of water, cooled in ice and filtered to yield 0.41 g (53%). Recrystallizion from 16 mL ethanol/water (3:1) resulted in 0.26 g (34% yield) 11-aminoundecanoic acid (mp. 189°-192° C., Lit. mp. 190°-192° C).

Workup

  1. temperatureThe mixture is refluxed for 17 hours
  2. filtrationThe neutralized solution is filtered
  3. customto remove any salt
  4. customto yield crude amino acid
  5. temperaturecooled in ice
  6. filtrationfiltered
  7. customto yield 0.41 g (53%)
  8. customRecrystallizion from 16 mL ethanol/water (3:1)

Sources & evidence

ORD record
ord-4b9421997b0b4777af1c8b709a2483d0
Source dataset
uspto-grants-1996_03
Patent number
US05498733

Reaction notes

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