Hydrochloric Acid → 12-[(2-Methylacryloyl)amino]dodecanoic acid

HRID 2399221Notes

Reaction equation

HRID 2399221 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].[OH-].[Na+].[CH3:18][C:19]([C:21](Cl)=[O:22])=[CH2:20].Cl>O.C(OCC)(=O)C>[C:21]([NH: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])(=[O:22])[C:19]([CH3:20])=[CH2:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 13528Methacryloyl chlorideHCID 14798Sodium HydroxideHCID 6966112-Aminododecanoic Acid

Product 1

HCID 1938658512-[(2-Methylacryloyl)amino]dodecanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
10 °C

Procedure

In 9 l of water at 30° C. were dissolved 218 g of 12-aminododecanoic acid and 100 g of sodium hydroxide (purity: 93%), and 102 ml of methacryl chloride was added thereto over 1 hour while stirring. The reaction mixture was stirred for 2 hours and then heated to 60° C., at which 3 l of ethyl acetate and 300 ml of concentrated hydrochloric acid were added thereto successively. The mixture was filtered while hot (60° C.) to remove any insoluble matter, followed by liquid-liquid separation. The organic layer was dried over 30 g of magnesium sulfate and, after removal of the magnesium sulfate, cooled to 10° C., at which 6 l of n-hexane was added, whereupon a precipitate was formed. The precipitate was collected by filtration and thoroughly washed with 1 l of n-hexane. Recrystallization of the precipitate from 500 ml of ethyl acetate yielded 128 g of 12-methacryloylaminododecanoic acid.

Workup

  1. additionwas added
  2. stirringThe reaction mixture was stirred for 2 hours
  3. additionwere added
  4. filtrationThe mixture was filtered while hot (60° C.)
  5. customto remove any insoluble matter
  6. customfollowed by liquid-liquid separation
  7. dry with materialThe organic layer was dried over 30 g of magnesium sulfate
  8. customafter removal of the magnesium sulfate
  9. additionwas added, whereupon a precipitate
  10. customwas formed
  11. filtrationThe precipitate was collected by filtration
  12. washthoroughly washed with 1 l of n-hexane
  13. customRecrystallization of the precipitate from 500 ml of ethyl acetate

Sources & evidence

ORD record
ord-4e26a1c3337045149dc472bb5678f90b
Source dataset
uspto-grants-1995_09
Patent number
US05447818

Reaction notes

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