1,4-Dichlorobenzene → 4-(5-Hexenyl)-1-chlorobenzene

HRID 1588376

Reaktionsgleichung

Reaktionsgleichung von HRID 1588376
Cl[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][CH:3]=1.[Mg].Br[CH2:11][CH2:12][CH2:13][CH2:14][CH:15]=[CH2:16]>O1CCCC1>[CH2:16]([C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][CH:3]=1)[CH2:15][CH2:14][CH2:13][CH:12]=[CH2:11]

Komponenten

5

Edukt 3

HCID 46851,4-DichlorobenzeneHCID 759066-Bromo-1-hexeneHCID 5462224Magnesium

Produkt 1

HCID 116369934-(5-Hexenyl)-1-chlorobenzeneAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution containing 294 g (2 mol) of 1,4-dichlorobenzene in 500 ml of anhydrous tetrahydrofuran was added dropwise over a period of about 110 minutes under nitrogen at 80° C. to a stirred suspension containing 48.6 g (2.0 mol) of magnesium turnings. The mixture was subsequently heated for 2 hours at 80°-84° C., then decanted from the excess magnesium, and the resultant solution of the Grignard compound was added dropwise over a period of 30 minutes at 80° C. to a stirred solution containing 194 g (1.8 mol) of 6-bromo-1-hexene (Fluka GmbH, 7910 Neu-Ulm) in 200 ml of tetrahydrofuran. The mixture was then stirred for 4 hours at 80° C. and then poured onto ice. After acidification with hydrochloric acid, the mixture was extracted three times with a 1:1 mixture of diethyl ether/methyl tert-butyl ether, and the ether fractions were stirred thoroughly with activated charcoal and dried over sodium sulfate. The filtrate was evaporated, and the residue was fractionated. At a pressure of 13 hPa and a temperature of 116°-118° C., 156 g (corresponding to a yield of 40% of theory) of 4-(5-hexenyl)-1-chlorobenzene were obtained. 4-(8-Nonenyl)-1-chlorobenzene (b.p. 87° C. at 0.3 hPa), for example, can also be prepared in the same way.

Aufarbeitung

  1. additionwas added dropwise over a period of about 110 minutes under nitrogen at 80° C. to a stirred suspension
  2. temperatureThe mixture was subsequently heated for 2 hours at 80°-84° C.
  3. customdecanted from the excess magnesium
  4. additionthe resultant solution of the Grignard compound was added dropwise over a period of 30 minutes at 80° C. to a stirred solution
  5. additionpoured onto ice
  6. extractionAfter acidification with hydrochloric acid, the mixture was extracted three times
  7. additionwith a 1:1 mixture of diethyl ether/methyl tert-butyl ether
  8. stirringthe ether fractions were stirred thoroughly with activated charcoal
  9. dry with materialdried over sodium sulfate
  10. customThe filtrate was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-7a2d363789004cc18785c0225eb40f59
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05221759

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