反应详情

温度

0 °C

20.0 g (96.06 mmol) methyl (2E)-3-(4-hydroxy-3-methoxyphenyl)-2-propenoate, 16.6 g (100.9 mmol) 8-chlor-1-octanol and 27.7 g (105.7 mmol) of triphenylphosphine were dissolved in 400 ml of tetrahydrofurane. The colorless solution was subsequently cooled to 0° C. and 46.0 g (105.7 mmol) of a 40% solution of azodicarboxylic acid diethyl ester in toluene was added dropwise thereto over a period of 25 minutes. The mixture was subsequently allowed to react for 4 hours at 0° C. The reaction mixture reduced in volume by evaporation. The resulting residue was added to a mixture of methanol and water (3:2) and was then extracted with a mixture of tert.-butyl-methylether:hexane 1:1. The tert.-butyl-methylether:hexane phase was washed repeatedly with water, dried over magnesium sulfate, filtered and concentrated by rotary evaporation. The crude product was recrystallised from 2-propanol yielded 30.8 g (90%) methyl (2E)-3-{4-[(8-chloroctyl)oxy]-3-methoxyphenyl}-2-propenoate as white crystals.

1. customto react for 4 hours at 0° C
2. customThe reaction mixture reduced in volume by evaporation
3. additionThe resulting residue was added to a mixture of methanol and water (3:2)
4. extractionwas then extracted with a mixture of tert.-butyl-methylether:hexane 1:1
5. washThe tert.-butyl-methylether:hexane phase was washed repeatedly with water
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated by rotary evaporation
9. customThe crude product was recrystallised from 2-propanol