Ethanol → 2,4-Octanedione

HRID 1938568Notes

Reaction equation

HRID 1938568 reaction equation
CC1C=C(C)C=C(C)C=1C1(C([O-])=O)CC(C)C(C)N1[C:17](=[O:19])[CH3:18].[H-].[Na+].[CH2:25]([OH:27])[CH3:26].[H][H].[C:30]1([CH3:36])[CH:35]=[CH:34]C=CC=1>>[CH3:18][C:17](=[O:19])[CH2:26][C:25](=[O:27])[CH2:36][CH2:30][CH2:35][CH3:34]

Participants

6

Reactant 5

HCID 702EthanolHCID 1140Toluene2×HCID 24758Sodium hydrideHCID 86751690HCID 86751690, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 841922,4-Octanedione

Procedure

16 g (0.048 mol) of ethyl N-(2,4,6-trimethylphenyl-acetyl-4,5-dimethyl-pyrrolidine-2-carboxylate in 50 ml of absolute toluene are added dropwise to a boiling solution of 2 g (0.067 mol) of NaH in 50 ml of absolute toluene and the mixture is refluxed. The end of the reaction is determined by TLC monitoring. The mixture is subsequently allow to cool to room temperature, and absolute ethanol is added with cooling until hydrogen is no longer evolved. The reaction mixture is evaporated under reduced pressure, the residue is taken up in water, and the mixture is acidified at room temperature using concentrated hydrochloric acid. The precipitate is filtered off with suction and dried in vacuo at 70° C. over P2O5. Purification is effected by extracting by boiling with chloroform/methyl tert-butyl ether and ether/n-hexane. 6.2 g (45.3%) of theory of 3-(2,4,6-trimethylphenyl)-1-aza-7,8-dimethyl-bicyclo-(3.3.01.5)-octane-2,4-dione of a melting point of >220° C. are obtained.

Workup

  1. temperaturethe mixture is refluxed
  2. customThe reaction mixture is evaporated under reduced pressure
  3. customis acidified at room temperature
  4. filtrationThe precipitate is filtered off with suction
  5. dry with materialdried in vacuo at 70° C. over P2O5
  6. customPurification
  7. extractionby extracting

Sources & evidence

ORD record
ord-89b581d8154a448aaa4bcf9dd80b09eb
Source dataset
uspto-grants-1997_12
Patent number
US05693663

Reaction notes

Loading…