Lithium Hydroxide → HCID 11347881, compound

HRID 395939Notes

Reaction equation

HRID 395939 reaction equation
C([NH:4][C:5]([CH2:25][OH:26])([CH2:8][CH:9]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:13][CH:12]=1)[OH:10])[CH2:6][OH:7])(=O)C.[Li+].[OH-]>CO.O>[NH2:4][C:5]([CH2:8][CH:9]([OH:10])[C:11]1[CH:12]=[CH:13][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:15][CH:16]=1)([CH2:6][OH:7])[CH2:25][OH:26]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 11303057HCID 11303057, compound

Product 1

HCID 11347881HCID 11347881, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2-Acetamido-4-(4-octylphenyl)-2-hydroxymethylbutane-1,4-diol (21′) (0.73 g) is dissolved in methanol (10 ml). Thereto is added a solution of LiOH (0.86 g) in water (10 ml), and the mixture is refluxed under heating for 2 hr. The reaction mixture is cooled and extracted with ethyl acetate. The organic layer is washed with brine and dried over sodium sulfate. The solvent is distilled away and the mixture is purified by silica gel column chromatography to give the title compound (22) as a colorless and amorphous powder. The resulting Compound (22) has the same physico-chemical characteristics as indicated in Example 2.

Workup

  1. temperaturethe mixture is refluxed
  2. temperatureunder heating for 2 hr
  3. temperatureThe reaction mixture is cooled
  4. extractionextracted with ethyl acetate
  5. washThe organic layer is washed with brine
  6. dry with materialdried over sodium sulfate
  7. distillationThe solvent is distilled away
  8. customthe mixture is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2c2722752da2412696a8fce894f81f26
Source dataset
uspto-grants-2003_08
Patent number
US06605744B2

Reaction notes

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