1-Ethynyl-2-methoxybenzene → 1-Methoxy-2-(1-octynyl)-benzene

Temperatur

-70 °C

2-Methoxyphenyl acetylene (9.00 g, 0.068M, Literature reference J. Villieras et al, Synthesis 459, 1975), was dissolved in dry, deaerated tetrahydrofuran/diethyl ether 1:1 (200 ml) and the solution stirred at -70° C. n-Butyl lithium 1.565M in hexane (43.5 ml, 0.068M) was added dropwise and the pale red mixture warmed to room temperature and stirred at that temperature for 15 min. The mixture was cooled to -70° C. and dry iodohexane (14.42 g, 0.068M) added dropwise. The white mixture was warmed to room temperature and stirred for 1 h, then refluxed for 4 h during which time a yellow solution formed. The reaction was cooled, poured into 1M sulphuric acid, (200 ml), and the product extracted with diethyl ether, (three times). The combined organic phases were washed with water, brine and dried, (MgSO4). Evaporation in vacuo yielded the crude produce as a pale yellow oil. Purification with column chromatography using silica gel and eluting with dichloromethane/n-hexane (1:3) gave 12.58 g (86%) of the title compound as a colourless oil.

1. customin dry
2. additionwas added dropwise
3. temperaturethe pale red mixture warmed to room temperature
4. stirringstirred at that temperature for 15 min
5. temperatureThe mixture was cooled to -70° C.
6. additiondry iodohexane (14.42 g, 0.068M) added dropwise
7. temperatureThe white mixture was warmed to room temperature
8. stirringstirred for 1 h
9. temperaturerefluxed for 4 h during which time a yellow solution
10. customformed
11. temperatureThe reaction was cooled
12. extractionthe product extracted with diethyl ether, (three times)
13. washThe combined organic phases were washed with water, brine
14. customdried
15. customEvaporation in vacuo
16. customyielded the crude
17. customproduce as a pale yellow oil
18. customPurification with column chromatography
19. washeluting with dichloromethane/n-hexane (1:3)

ORD-Eintrag

ord-50e6aef17878467eb85dc4dc4d668799

Quelldatensatz

uspto-grants-1987_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04713486