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

HRID 617577Notes

Reaction equation

HRID 617577 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-113326aed6cf43e9bf5b4ff7f4f7d30c
Source dataset
uspto-grants-1999_09
Patent number
US05948820

Reaction notes

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