Iodine → 1,1-Di(p-tolyl)ethylene

HRID 1597736

反応式

HRID 1597736 の反応式
[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

参加物

8

反応物 6

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

生成物 1

HCID 1377651,1-Di(p-tolyl)ethylene

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

15.6 g (0.65 mol) of magnesium and 20 ml of THF were placed in a 1-liter reaction flask in a stream of nitrogen, the reaction was initiated with a small amount of ethyl iodide and iodine, and a solution of 111.15 g (0.65 mol) of p-bromotoluene in 500 ml of THF was added dropwise at a temperature from room temperature to 40° C. for 2 hours to prepare a Grignard reagent. A solution of 83.75 g (0.625 mol) of p-methylacetophenone (11c) in 200 ml of THF was added dropwise thereto at the same temperature for 3 hours. The resulting solution was stirred at room temperature for 3 hours, and subsequently stirred under reflux for 4 hours. Then, the solution was cooled, and poured into 1 liter of 5% aqueous sulfuric acid to conduct hydrolysis. The resulting product was extracted with toluene, and the extract was washed with aqueous soda ash, washed with water, and concentrated. Then, 300 ml of toluene and 0.5 g of PTSA were added thereto, followed by stirring under reflux for 4 hours to carry out azeotropic dehydration. The resulting product was washed with aqueous soda ash, washed with water, and concentrated. Crude 1,1-di(p-tolyl)ethylene (9c) was distilled in a Claisen flask equipped with a vigreux to obtain 98.5 g.

後処理

  1. stirringsubsequently stirred
  2. temperatureunder reflux for 4 hours
  3. temperatureThen, the solution was cooled
  4. customhydrolysis
  5. extractionThe resulting product was extracted with toluene
  6. washthe extract was washed with aqueous soda ash
  7. washwashed with water
  8. concentrationconcentrated
  9. additionThen, 300 ml of toluene and 0.5 g of PTSA were added
  10. stirringby stirring
  11. temperatureunder reflux for 4 hours
  12. washThe resulting product was washed with aqueous soda ash
  13. washwashed with water
  14. concentrationconcentrated
  15. distillationCrude 1,1-di(p-tolyl)ethylene (9c) was distilled in a Claisen flask
  16. customequipped with a vigreux
  17. customto obtain 98.5 g

出典と根拠

ORDレコード
ord-f3012dea11b54feba994cbfa04ab3b5d
出典データセット
uspto-grants-1998_04
特許番号
US05736284

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