Sodium Hydroxide → HCID 19764428, compound

HRID 247834Notes

Reaction equation

HRID 247834 reaction equation
[CH3:1][CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[NH:13][C:14](=[O:20])[CH2:15][O:16]C(=O)C)[CH3:3].[OH-].[Na+]>CO>[CH3:3][CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:11])[CH3:12])[C:5]=1[NH:13][C:14](=[O:20])[CH2:15][OH:16])[CH3:1]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 2524544HCID 2524544, compound

Product 1

HCID 19764428HCID 19764428, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-[2,6-bis(1-methylethyl)phenyl]-2-acetoxyacetamide (Example N) (5.7 g, 20.6 mmol) in methanol (50 mL) is added 2M sodium hydroxide solution (20 mL). The solution is stirred at room temperature for 1 hour. The mixture is concentrated, diluted with water, and extracted three times with ethyl acetate. The combined organic extracts are washed with brine, dried over magnesium sulfate, and concentrated to afford 4.6 g of the title compound as an off-white solid; mp 164°-166° C.

Workup

  1. concentrationThe mixture is concentrated
  2. additiondiluted with water
  3. extractionextracted three times with ethyl acetate
  4. washThe combined organic extracts are washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7c62d0e66f8e40dfb214a9d7f9fcc3fa
Source dataset
uspto-grants-1993_05
Patent number
US05208224

Reaction notes

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