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

Temperature

80 °C

A solution containing 294 g (2 mol) of 1,4-dichlorobenzene in 500 ml of anhydrous tetrahydrofuran was added dropwise under nitrogen at 80° C. to a stirred suspension of 48.6 g (2.0 mol) of magnesium turnings over the course of 110 min. The mixture was then heated at 80°-84° C. for 2 hours, and the solution of the Grignard compound was decanted off the excess magnesium and added dropwise at 80° C. over the course of 30 min to a stirred solution containing 194 g (1.8 mol) of 6-bromo-1-hexene (available from Fluka GmbH, D-7910 Neu-Ulm) in 200 ml of tetrahydrofuran. The mixture was then stirred at 80° C. for 4 hours and poured onto ice. Acidification with hydrochloric acid was followed by extraction three times with a 1:1 diethyl ether/methyl tert-butyl ether mixture, and the ether fractions were stirred with active carbon and dried over sodium sulfate. The residue after concentration of the filtrate was fractionated under reduced pressure. About 156 g (corresponding to a yield of 40% of theory) of 4-(5-hexenyl)-1-chlorobenzene were obtained at a temperature of 116°-118° C. under a pressure of 13 hPa.

1. temperatureThe mixture was then heated at 80°-84° C. for 2 hours
2. customthe solution of the Grignard compound was decanted off the excess magnesium
3. additionadded dropwise at 80° C. over the course of 30 min to a stirred solution
4. additionpoured onto ice
5. extractionAcidification with hydrochloric acid was followed by extraction three times with a 1:1 diethyl ether/methyl tert-butyl ether mixture
6. stirringthe ether fractions were stirred with active carbon
7. dry with materialdried over sodium sulfate

ORD record

ord-02c64e25e6ce499182b9dbf18c8a79ce

Source dataset

uspto-grants-1995_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05399290