1-Chloroheptane → Heptylbenzene

HRID 1645689

Reaktionsgleichung

Reaktionsgleichung von HRID 1645689
[CH2:1](Cl)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[C:9]1([Mg]Cl)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Cl-].[NH4+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1([B-](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1([PH+](C2CCCCC2)C2CCCCC2)CCCCC1.O1CCCC1.CN1CCCC1=O>[C:9]1([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

8

Edukt 3

HCID 123711-ChloroheptaneHCID 25517Ammonium ChlorideHCID 178478979HCID 178478979, Verbindung

Produkt 1

HCID 14115Heptylbenzene

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845palladium(II) acetateKatalysatorHCID 23136635Tricyclohexylphosphonium tetraphenylborateKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

A 30-ml four-necked flask was equipped with a stirrer, a thermometer, a dropping funnel and a reflux condenser. 0.027 g (0.12 mmol) of palladium (II) acetate and 7 ml of N-methylpyrrolidinone were weighed in the flask, followed by, stirring. Further, 0.072 g (0.12 mmol) of tricyclohexylphosphonium tetraphenylborate obtained in Example A-4 was weighed in air and added into the flask. The flask was purged with argon, followed by stirring at 25° C. for 30 minutes. 0.404 g (3 mmol) of n-heptyl chloride was added, followed by stirring at 25° C. for 30 minutes. 2 ml (4.4 mmol) of 2.2M tetrahydrofuran solution of phenylmagnesium chloride was added dropwise at 25° C. over a period of 10 minutes, followed by stirring at 25° C. for 19 hours. After the completion of the reaction, 6 ml of tetrahydrofuran and 10 ml of saturated aqueous ammonium chloride solution were added, followed by separation. The organic phase was purified by column chromatography to afford 0.435 g of 1-phenylheptane (yield: 82 mol % based on n-heptyl chloride). The identification of the product was made by mass spectroscopy.

Aufarbeitung

  1. customA 30-ml four-necked flask was equipped with a stirrer
  2. additionadded into the flask
  3. customThe flask was purged with argon
  4. stirringby stirring at 25° C. for 30 minutes
  5. stirringby stirring at 25° C. for 30 minutes
  6. stirringby stirring at 25° C. for 19 hours
  7. additionwere added
  8. customfollowed by separation
  9. customThe organic phase was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-db72be0193de45f19ebe8a185bc5df20
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08124809B2

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