Toluene → 1-(2,4,6-Trimethyl-3-pyridinyl)-1,3-butanedione

HRID 918064Notes

Reaction equation

HRID 918064 reaction equation
[C:1]([C:4]1[C:5]([CH3:12])=[N:6][C:7]([CH3:11])=[CH:8][C:9]=1[CH3:10])(=[O:3])[CH3:2].C1(C)C=CC=CC=1.[C:20](OCC)(=[O:22])[CH3:21]>C(O)(=O)C>[CH3:12][C:5]1[N:6]=[C:7]([CH3:11])[CH:8]=[C:9]([CH3:10])[C:4]=1[C:1]([CH2:2][C:20](=[O:22])[CH3:21])=[O:3]

Participants

5

Reactant 3

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 2681243-Acetyl-2,4,6-trimethylpyridine

Product 1

HCID 537711251-(2,4,6-Trimethyl-3-pyridinyl)-1,3-butanedioneYield 86%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 172.0 g of 3-acetyl-collidine, 4.5 l of anhydrous toluene, 195 g of ethyl acetate and 282.5 g of potassium tert.-butylate is heated at 100° for 4 hours under nitrogen. The reaction mixture is cooled and poured into 1/2 l of ice water and 140 ml of acetic acid, and the phases are separated and worked up in the customary manner to give 186.1 g of 2,4,6-trimethyl-nicotinoyl-acetone ##SPC8##

Workup

  1. temperatureis heated at 100° for 4 hours under nitrogen
  2. temperatureThe reaction mixture is cooled
  3. customthe phases are separated

Sources & evidence

ORD record
ord-6c881ff38ad5451ca864df52c054bf45
Source dataset
uspto-grants-1976_07
Patent number
US03969363

Reaction notes

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