Ammonium Chloride → 3-Amino-3-[2-(4-octylphenyl)ethyl]hexane-1,6-diol

HRID 842261Notes

Reaction equation

HRID 842261 reaction equation
C([O:4][CH2:5][CH2:6][C:7]([NH:31]C(=O)C)([CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:19][CH:18]=1)[CH2:8][CH2:9][CH2:10][O:11]C(=O)C)(=O)C.O.[OH-].[Li+].[Cl-].[NH4+]>CO.O>[NH2:31][C:7]([CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:19][CH:18]=1)([CH2:8][CH2:9][CH2:10][OH:11])[CH2:6][CH2:5][OH:4]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 168937Lithium hydroxide, monohydrateHCID 10648237HCID 10648237, compound

Product 1

HCID 158641333-Amino-3-[2-(4-octylphenyl)ethyl]hexane-1,6-diolYield 98.7%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of 3-acetamido-6-acetoxy-3-[2-(4-octylphenyl)ethyl]hexyl acetate (400 mg) in methanol-water (1:1) (12 ml), lithium hydroxide monohydrate (360 mg) was added at room temperature and the mixture was refluxed under heating for 4 hours. After cooling, the mixture was neutralized with ammonium chloride and the solvent was distilled away under reduced pressure. The residue obtained was extracted with chloroform, the extract was washed with water and a saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled away to give the subject compound (290 mg) as a yellowish oily substance.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 4 hours
  3. temperatureAfter cooling
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe residue obtained
  6. extractionwas extracted with chloroform
  7. washthe extract was washed with water
  8. dry with materiala saturated brine and dried over anhydrous magnesium sulfate
  9. distillationThe solvent was distilled away

Sources & evidence

ORD record
ord-be5d4387163d42cbac5e23f09f2ce557
Source dataset
uspto-grants-2002_04
Patent number
US06372800B1

Reaction notes

Loading…