Iodine → 1,1-Di(p-tolyl)ethylene

HRID 1603409

Reaktionsgleichung

Reaktionsgleichung von HRID 1603409
[Mg].C(I)C.II.Br[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1.[CH3:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=O)[CH3:23])=[CH:18][CH:17]=1.S(=O)(=O)(O)O>C1COCC1>[C:11]1([CH3:14])[CH:12]=[CH:13][C:8]([C:22]([C:19]2[CH:20]=[CH:21][C:16]([CH3:15])=[CH:17][CH:18]=2)=[CH2:23])=[CH:9][CH:10]=1

Komponenten

8

Edukt 6

HCID 807IodineHCID 1118Sulfuric AcidHCID 6340IodoethaneHCID 78054-BromotolueneHCID 8500p-METHYLACETOPHENONEHCID 5462224Magnesium

Produkt 1

HCID 1377651,1-Di(p-tolyl)ethyleneAusbeute 75,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

Into a 1-liter reaction flask were introduced in a nitrogen stream 15.6 g (0.65 mol) of magnesium and 20 ml of THF. Slight amounts of ethyl iodide and iodine were added thereto to initiate reaction. A solution of 111.15 g (0.65 mol) of p-bromotoluene in 500 ml of THF was then added dropwise at room temperature to 40° C. over a period of 2 hours to prepare a Grignard reagent. Thereto was added dropwise a solution of 83.75 g (0.625 mol) of p-methylacetophenone (10a) in 200 ml of THF at that temperature over a period of 3 hours. This mixture was stirred first at room temperature for 3 hours and then with refluxing for 4 hours. The resulting reaction mixture was cooled and poured into 1 liter of 5% aqueous sulfuric acid solution to conduct hydrolysis. This mixture was extracted with toluene, and the extract was washed with aqueous soda ash solution and then with water and concentrated. Thereto were added 300 ml of toluene and 0.5 g of PTSA. The resulting mixture was stirred with refluxing for 4 hours to conduct azeotropic dehydration, followed by washing with aqueous soda ash solution, washing with water, and concentration. The resulting crude 1,1-di(p-tolyl)ethylene (9b) was distilled with a Claisen flask equipped with a vigreux, giving 98.5 g of the desired compound.

Aufarbeitung

  1. customInto a 1-liter reaction flask
  2. customreaction
  3. temperaturewith refluxing for 4 hours
  4. customThe resulting reaction mixture
  5. temperaturewas cooled
  6. customhydrolysis
  7. extractionThis mixture was extracted with toluene
  8. washthe extract was washed with aqueous soda ash solution
  9. concentrationwith water and concentrated
  10. additionThereto were added 300 ml of toluene and 0.5 g of PTSA
  11. stirringThe resulting mixture was stirred
  12. temperaturewith refluxing for 4 hours
  13. washby washing with aqueous soda ash solution
  14. washwashing with water, and concentration
  15. distillationThe resulting crude 1,1-di(p-tolyl)ethylene (9b) was distilled with a Claisen flask
  16. customequipped with a vigreux

Quellen und Nachweise

ORD-Eintrag
ord-a7c5887422cf4bf4b847c2d10fffa735
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05989765

Verknüpfte Notizen

Wird geladen…