Methanol → Methyl 12-aminododecanoate

HRID 1291689

Reaction equation

HRID 1291689 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14].CO.S(=O)(=O)(O)O.[C:23](=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:23])=[O:14]

Participants

6

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 6966112-Aminododecanoic Acid

Product 1

HCID 3665980Methyl 12-aminododecanoateYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a 3-l flask equipped with a stirrer, 200.0 g (0.93 mol) of 12-aminododecanoic acid, 600 g of methanol and 100 g (1.0 mol) of sulfuric acid were charged, followed by stirring at 60° C. for 5 hours. After the reaction mixture was allowed to cool down, it was diluted with methylene chloride, followed by neutralization with an aqueous solution of sodium carbonate. The solvent was distilled off under reduced pressure, followed by purification by chromatography on an alumina short column, whereby 201.7 g of the title compound (7-a) were obtained (yield: 95%).

Workup

  1. customTo a 3-l flask equipped with a stirrer
  2. temperatureto cool down
  3. distillationThe solvent was distilled off under reduced pressure
  4. customfollowed by purification by chromatography on an alumina short column

Sources & evidence

ORD record
ord-65d1920ed434425f8e8e578931e129a0
Source dataset
uspto-grants-1998_05
Patent number
US05753707

Linked notes

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