Diethyl Ether → 1-(3-Vinylphenyl)-1-phenylethane
Reaction equation
Cl[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:3].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOCC.[CH:44]([C:46]1[CH:47]=[C:48]([Mg]Br)[CH:49]=[CH:50][CH:51]=1)=[CH2:45]>[Ni](Cl)Cl.O>[CH:2]([C:4]1[CH:9]=[C:8]([CH:44]([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[CH3:45])[CH:7]=[CH:6][CH:5]=1)=[CH2:3]Participants
Conditions
- Temperature
- 0 °C
Procedure
Then, 94 g (0.67 mole) of (1-chloroethyl)benzene of the formula (VI) and 5.4 g of the catalyst of nickel chloride (II) with ligands of 1,3-bis(diphenylphosphino)propane were mixed into 500 ml of dried ether. The above Grignard reagent was dropped little by little into this mixture over 2 hours. During the dropping, the temperature in the reactor was maintained at 0° C. After the dropping, stirring was continued for further 24 hours. The reaction mixture was then poured into iced water (1000 g of ice and 500 g of water) and aqueous layer and oily layer were separated to recover the oily layer. After that, ether and tetrahydrofuran were evaporated off under a reduced pressure to obtain 1-(3-vinylphenyl)-1-phenylethane in a yield of 74%.
Workup
- customwere separated
- customto recover the oily layer
- customAfter that, ether and tetrahydrofuran were evaporated off under a reduced pressure
Sources & evidence
- ORD record
- ord-e283a0178b0546fdac8e0a03954aff74
- Source dataset
- uspto-grants-1989_04
- Patent number
- US04822934
Reaction notes
Loading…