Allyl bromide → 1-Methoxy-4-(pent-4-en-1-yl)benzene

A solution containing 4-methoxyphenethyl magnesium iodide (prepared from 60 g, 0.23 mol of 4-methoxyphenethyl iodide and excess magnesium turnings) in anhydrous tetrahydrofuran (200 ml) at 0° C. under a nitrogen atmosphere was treated with 3-bromoprop-1-ene (46.7 g, 0.33 mol) and then stirred at room temperature for 14 hours. The resulting solution was washed with saturated aqueous ammonium chloride solution (3×100 ml) and the aqueous washings were back extracted with dichloromethane (3×100 ml). The tetrahydrofuran and dichloromethane solutions were combined, washed with aqueous sodium thiosulphate solution, dried (MgSO4) and the solvent was evaporated off under reduced pressure to yield an oil which was distilled to yield 5-(4-methoxyphenyl)pent-1-ene as a pale yellow oil (b.p. 65° C., 0.3 mm. Hg) having the following structural characteristics:

1. washThe resulting solution was washed with saturated aqueous ammonium chloride solution (3×100 ml)
2. extractionthe aqueous washings were back extracted with dichloromethane (3×100 ml)
3. washwashed with aqueous sodium thiosulphate solution
4. dry with materialdried (MgSO4)
5. customthe solvent was evaporated off under reduced pressure
6. customto yield an oil which
7. distillationwas distilled

ORD record

ord-598957fca71a4cf9809d3130f6fc832b

Source dataset

uspto-grants-1989_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04837333