Sodium Iodide → 2,3-Diphenyl-1,3-butadiene

HRID 978909Notes

Reaction equation

HRID 978909 reaction equation
Br[CH2:2][C:3]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[C:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:5]Br.[Na+].[I-]>CC(C)=O>[C:7]1([C:4]([C:3]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH2:2])=[CH2:5])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 540340061,1'-(1,4-Dibromobut-2-ene-2,3-diyl)dibenzene

Product 1

HCID 41291332,3-Diphenyl-1,3-butadiene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The process of this invention for synthesis of 2,3-diphenyl-1,3-butadiene is comprised of a four step procedure wherein the starting compound acetophenone is dimerized under an ultra violet reaction process to yield acetophenone pinacol which is subsequently converted to 2,3-diphenyl-2-butene in the step 2 procedure. The 2,3-diphenyl-2-butene is then reacted with N-bromosuccinimide (NBS) in an ultra violet reactor in a CCl4 reaction solvent to form 1,4-dibromo-2,3-diphenyl-2-butene in the step 3 procedure. The 1,4-dibromo-2,3-diphenyl-2-butene is reacted with NaI in a hot acetone solution to yield 2,3-diphenyl-1,3-butadiene in the step 4 procedure.

Sources & evidence

ORD record
ord-5b3df1e38e1a4f6981f211a9861351a5
Source dataset
uspto-grants-1987_05
Patent number
US04665257

Reaction notes

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