Acetone → HCID 20402715, compound

HRID 544104Notes

Reaction equation

HRID 544104 reaction equation
[CH3:1][O:2][C:3]([CH:5]([N:7]([C:21](=[O:25])[CH2:22][O:23][CH3:24])[C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]([CH2:15][O:16]C(=O)C)[C:9]=1[CH3:20])[CH3:6])=[O:4].[OH-].[Na+].CC(C)=O>O>[CH3:1][O:2][C:3]([CH:5]([N:7]([C:21](=[O:25])[CH2:22][O:23][CH3:24])[C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]([CH2:15][OH:16])[C:9]=1[CH3:20])[CH3:6])=[O:4]

Participants

5

Reactant 3

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 20402713HCID 20402713, compound

Product 1

HCID 20402715HCID 20402715, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

23.0 g of N-(1'-methoxycarbonyl-ethyl)-N-methoxyacetyl-2,6-dimethyl-3-acetoxymethylaniline, 9.2 g of 30% sodium hydroxide solution and 100 ml of acetone were stirred for 3 hours at room temperature; 20 ml of water were then added, and the reaction mixture was extracted twice with 50 ml of diethyl ether each time. The combined ether extracts were dried over sodium sulfate, and the solvent was evaporated off. The oily crude product was chromatographed through a silica gel column by means of ether/chloroform (1:1) to thus obtain the product in the form of colourless oil: nD14 =1.5352.

Workup

  1. extractionthe reaction mixture was extracted twice with 50 ml of diethyl ether each time
  2. dry with materialThe combined ether extracts were dried over sodium sulfate
  3. customthe solvent was evaporated off
  4. customThe oily crude product was chromatographed through a silica gel column by means of ether/chloroform (1:1)
  5. customto thus obtain the product in the form of colourless oil

Sources & evidence

ORD record
ord-89070db6ba0b4c4689d34e9ebccb617a
Source dataset
uspto-grants-1984_05
Patent number
US04448773

Reaction notes

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