Ethyl Bromide → Ethyl alpha-[p-(3-methyl-2-butenyl)phenyl]propionate

HRID 1388803

Reaktionsgleichung

Reaktionsgleichung von HRID 1388803
C(Br)C.[Mg].Cl[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])=[CH:8][CH:7]=1.Br[CH:18]([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20].[Cl-].[NH4+]>[Ni](Cl)Cl.C1COCC1>[CH2:12]([C:9]1[CH:10]=[CH:11][C:6]([CH:18]([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:7][CH:8]=1)[CH:13]=[C:14]([CH3:16])[CH3:15]

Komponenten

8

Edukt 5

HCID 6332Ethyl BromideHCID 25517Ammonium ChlorideHCID 79040Ethyl 2-bromopropionateHCID 316460p-ChloroprenylbenzeneHCID 5462224Magnesium

Produkt 1

HCID 13118083Ethyl alpha-[p-(3-methyl-2-butenyl)phenyl]propionateAusbeute 49,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24385Nickel DichlorideKatalysatorHCID 8028TetrahydrofuranLösungsmittel5×

Versuchsvorschrift

Under a nitrogen atmosphere, 0.3 ml of ethyl bromide was added to a mixture of 0.97 g of magnesium turning for Grignard reaction and 2 ml of THF. After the starting of the reaction, a solution composed of 6.01 g of p-chloroprenylbenzene and 1 ml of THF was added dropwise while maintaining the temperature at 115° to 130° C. After the addition, THF was added further as required, and the mixture was stirred at 110° to 120° C. for 4 hours. After cooling, 20 ml of THF was further added, and the resulting reaction mixture was added dropwise to a solution composed of 5.43 g of ethyl α-bromopropionate, 0.016 g of nickel chloride and 5 ml of THF. After the addition, the mixture was further stirred for 1 hour, and an aqueous solution of ammonium chloride was added. The mixture was extracted with diethyl ether. The ethereal extract was washed with an aqueous solution of sodium chloride, dried, concentrated and distilled to give 3.62 g (yield 49.1%) of ethyl α-(p-prenylphenyl)propionate.

Aufarbeitung

  1. customAfter the starting of the reaction
  2. additionwas added dropwise
  3. temperaturewhile maintaining the temperature at 115° to 130° C
  4. additionwas added further
  5. temperatureAfter cooling
  6. customthe resulting reaction mixture
  7. additionwas added dropwise to a solution
  8. additionAfter the addition
  9. stirringthe mixture was further stirred for 1 hour
  10. extractionThe mixture was extracted with diethyl ether
  11. extractionThe ethereal extract
  12. washwas washed with an aqueous solution of sodium chloride
  13. customdried
  14. concentrationconcentrated
  15. distillationdistilled

Quellen und Nachweise

ORD-Eintrag
ord-df554f621f6543b3aff215019144c817
Quelldatensatz
uspto-grants-1984_02
Patentnummer
US04433160

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