Acetic Acid → HCID 53800728, compound

HRID 1277349Notes

Reaction equation

HRID 1277349 reaction equation
[C:1]([CH2:4][C:5](=[O:7])[CH3:6])(=[O:3])[CH3:2].[CH2:8]([O:10][CH:11](OCC)OCC)[CH3:9].C(OC(=O)C)(=O)C.C(O)(=O)C>C(O)C>[CH2:8]([O:10][CH:11]=[CH:2][C:1]([CH2:4][C:5](=[O:7])[CH3:6])=[O:3])[CH3:9]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 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 orthoformic acidtriethyl 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-a84b2e10c287414d8c26ff289c58b141
Source dataset
uspto-grants-1981_07
Patent number
US04277418

Reaction notes

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