Methanol → 12-Aminododecanoic Acid

HRID 260938Notes

Reaction equation

HRID 260938 reaction equation
[O:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13](=[N:15]O)O.[H][H].C[OH:20]>[Pt]=O>[NH2:15][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]([OH:20])=[O:1]

Participants

5

Reactant 3

HCID 887Methanol2×HCID 178418361HCID 178418361, compoundHCID 178520596HCID 178520596, compound

Product 1

HCID 6966112-Aminododecanoic AcidYield 92%

Reagents, catalysts & solvents 1

HCID 82844Platinum oxide (PtO)Catalyst

Procedure

In a paar hydrogenation bottle was placed 0.92 g (4×10-3 mol) 12-oxododecanoic acid oxime, 10 mL methanol, and then 0.005 g (2.2×10-5 mol) platinum oxide (Adam's catalyst). The bottle was fitted to a paar high-pressure system, deaerated, deaerated, then filled with hydrogen gas to maintain a pressure of about 3 atm for 1.5 hours with continuous shaking. After hydrogenation, 10 mL of methanol was added to the reaction mixture, then heated to gentle boiling to dissolve the product. The hot mixture was quickly filtered to remove suspension of black platinum, after which the filtrate on evaporation gave 0.85 g (92% yield) 12-aminododecanoic acid. Recrystallization was effected with ethanol/water mixture (1:1) to give 0.80 g (87% yield) 12-aminododecanoic acid (m.p. 184°-186° C., Lit. 185°-187° C.).

Workup

  1. customThe bottle was fitted to a paar high-pressure system
  2. temperatureto maintain a pressure of about 3 atm for 1.5 hours with continuous shaking
  3. temperatureheated to gentle boiling
  4. dissolutionto dissolve the product
  5. filtrationThe hot mixture was quickly filtered
  6. customto remove
  7. additionsuspension of black platinum
  8. customafter which the filtrate on evaporation

Sources & evidence

ORD record
ord-e63459e9ae694a3aa7ff3b40e81946ec
Source dataset
uspto-grants-1996_06
Patent number
US05530148

Reaction notes

Loading…