Hydroquinone → N-Octyl-beta-alanine

HRID 65420

Reaction equation

HRID 65420 reaction equation
[CH2:1]([NH2:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C1(C=CC(O)=CC=1)O.[C:18]([OH:22])(=[O:21])[CH:19]=[CH2:20].[OH-].[Na+]>CC(C)=O.CO>[CH2:1]([NH:9][CH2:20][CH2:19][C:18]([OH:22])=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 4

HCID 785HydroquinoneHCID 6581Acrylic AcidHCID 8143OctylamineHCID 14798Sodium Hydroxide

Product 1

HCID 13765821N-Octyl-beta-alanineYield 78%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 887MethanolSolvent

Procedure

To a mixture of n-octylamine (516 g, 4.0 mols), hydroquinone (200 mg) and methanol (400 ml), acrylic acid (144 g, 2.0 mols) was added dropwise with stirring while cooling with ice. After addition, the mixture was refluxed while heating for 4 hours. After cooled to room temperature, NaOH (80 g, 2.0 mols) was added. The reaction mixture was despersed in 6 liters of acetone, and filtration and drying were carried out to obtain the Na salt of N-n-octyl-β-alanine as white crystals having a melting point (dec.) of 242° C. (349 g Yield: 78%).

Workup

  1. additionwas added dropwise
  2. temperaturewhile cooling with ice
  3. additionAfter addition
  4. temperaturethe mixture was refluxed
  5. temperaturewhile heating for 4 hours
  6. filtrationfiltration
  7. customdrying

Sources & evidence

ORD record
ord-5e8802d8235240cab6cb20b4167dd222
Source dataset
uspto-grants-1986_09
Patent number
US04614699

Linked notes

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