Lithium hydroxide, monohydrate → HCID 15864131, compound

HRID 617572Notes

Reaction equation

HRID 617572 reaction equation
C([O:4][CH2:5][CH2:6][C:7]([NH:33]C(=O)C)([CH2:28][O:29]C(=O)C)[CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:13][CH:12]=1)(=O)C.O.[OH-].[Li+]>CO.O>[NH2:33][C:7]([CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:13][CH:12]=1)([CH2:6][CH2:5][OH:4])[CH2:28][OH:29]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 15864135HCID 15864135, compound

Product 1

HCID 15864131HCID 15864131, compoundYield 25.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

3-Acetamido-3-acetoxymethyl-6-(4-undecylphenyl)hexyl acetate (1.70 g) and lithium hydroxide monohydrate (1.42 g) were dissolved in methanol (17 ml) and water (17 ml), and the mixture was refluxed under heating for 3 hours while stirring. The reaction mixture was diluted with water (100 ml) and extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate and the solvent was distilled away. The crude crystals obtained were recrystallized from ether-hexane-ethyl acetate (2:2:1) to give the subject compound (330 mg) as white crystals, melting at 73-76° C.

Workup

  1. temperatureunder heating for 3 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled away
  5. customThe crude crystals obtained
  6. customwere recrystallized from ether-hexane-ethyl acetate (2:2:1)

Sources & evidence

ORD record
ord-b5d628366d8c41feba032a7590a4838f
Source dataset
uspto-grants-1999_09
Patent number
US05948820

Reaction notes

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