monoacetoacetin → Glycerol bis-acetoacetate

HRID 37607Notes

Reaction equation

HRID 37607 reaction equation
[CH3:1][C:2]([CH2:4][C:5]([OH:7])=[O:6])=[O:3].[CH2:8]([OH:13])[CH:9]([OH:12])[CH2:10]O>C(OCC)(=O)C>[C:5]([O:7][CH2:10][CH:9]([CH2:8][OH:13])[O:12][C:5](=[O:6])[CH2:4][C:2]([CH3:1])=[O:3])(=[O:6])[CH2:4][C:2]([CH3:1])=[O:3]

Participants

3

Reactant 1

HCID 125624monoacetoacetin

Product 1

HCID 9878359Glycerol bis-acetoacetate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A portion of the crude reaction product (3600 g) was dissolved in approximately 6 liters of ethyl acetate and extracted with distilled water (3×3 L) to provide a first aqueous fraction and again extracted with water (6× 3 L) to provide a second aqueous fraction. Analysis of the aqueous extracts by HPLC indicated that essentially all of the monoacetoacetin contained in the crude reaction product was removed in the first aqueous fraction. Using a freeze-dryer, water was removed from the second aqueous fraction until constant weight was achieved (1029.5 g, ca. 30%). This material was tested without further purification for efficacy as a parenteral nutrient.

Workup

  1. extractionextracted with distilled water (3×3 L)
  2. customto provide a first aqueous fraction
  3. extractionagain extracted with water (6× 3 L)
  4. customto provide a second aqueous fraction
  5. customreaction product
  6. customwas removed in the first aqueous fraction
  7. customwas removed from the second aqueous fraction until constant weight
  8. customThis material was tested without further purification for efficacy as a parenteral nutrient

Sources & evidence

ORD record
ord-3176373fc9974170acca419604b9dcc2
Source dataset
uspto-grants-1995_05
Patent number
US05420335

Reaction notes

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