Acetic Acid → HCID 53800728, compound

HRID 358432Notes

Reaction equation

HRID 358432 reaction equation
[C:1]([CH2:4][C:5](=[O:7])[CH3:6])(=[O:3])[CH3:2].[C:8]([O:11][C:12](=O)C)(=O)[CH3:9].C(O)(=O)C>C(O)C>[CH2:8]([O:11][CH:12]=[CH:2][C:1]([CH2:4][C:5](=[O:7])[CH3:6])=[O:3])[CH3:9]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 31261Acetylacetone

Product 1

HCID 53800728HCID 53800728, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

253 g (2.5 moles) of acetylacetone, 1,110 g (7.5 moles) of orthformic acid triethyl ester and 8 g of acetic anhydride are heated to ebullition in a flask with vigorous stirring. During the reaction, about 23 g of acetic acid is added and the ethanol formed is distilled off. After 2 to 3 hours the reaction is completed. The unreacted orthoformic acid triethyl ester is distilled out at reduced pressure (5 to 1 Torr) through the top of the column and fed back to the next batch. Following this, 355 g of ethoxymethylene acetylacetone is evaporated, separated from the residue through a simple distillation bridge at 0.1 to 0.3 Torr. The yield, referred to acetylacetone, was 91% of theory.

Workup

  1. customto ebullition in a flask with vigorous stirring
  2. additionis added
  3. distillationis distilled off
  4. distillationThe unreacted orthoformic acid triethyl ester is distilled out at reduced pressure (5 to 1 Torr) through the top of the column
  5. customis evaporated
  6. customseparated from the residue through a simple distillation bridge at 0.1 to 0.3 Torr

Sources & evidence

ORD record
ord-7b7437000ed34255b0f5ca6f23ed94a6
Source dataset
uspto-grants-1984_08
Patent number
US04468353

Reaction notes

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