Benzaldehyde → 1,1-Diphenylethylene

HRID 2164695Notes

Reaction equation

HRID 2164695 reaction equation
[BH4-].[Na+].[C:3]1([CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17](=O)[CH3:18])[CH3:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:20][Mg]I.C(=O)C1C=CC=CC=1.C([Mg]Br)C1C=CC=CC=1.[C:40]1([CH:46]=[C:47]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH3:48])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.C1(C(C2C=CC=CC=2)=O)C=CC=CC=1>>[C:3]1([CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]([CH3:18])=[CH2:20])[CH3:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:40]1([CH:46]=[CH:47][C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.[C:49]1([C:47]([C:46]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:40]=2)=[CH2:48])[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1

Participants

10

Reactant 7

HCID 240BenzaldehydeHCID 3102BenzophenoneHCID 130701,2-Diphenyl-1-propeneHCID 4311764Sodium borohydrideHCID 20069224HCID 20069224, compoundHCID 178418373HCID 178418373, compound2×HCID 178419663HCID 178419663, compound

Product 3

HCID 107401,1-DiphenylethyleneHCID 11502StilbeneHCID 20069234Phenyl(isopropenylphenyl)ethane

Procedure

For instance, vinylnaphthalene is prepared by reacting formylnaphthalene with a Grignard reagent such as methylmagnesium iodide, and then dehydrating. Phenyl(vinylphenyl)ethane is prepared by reacting diphenylethane with acetyl chloride in the presence of a Friedel-Crafts catalyst to obtain phenyl(acetylphenyl)ethane, reducing by sodium borohydride, and then dehydrating. Phenyl(isopropenylphenyl)ethane is prepared by reacting phenyl(acetylphenyl)ethane with a Grignard reagent such as methylmagnesium iodide, and then dehydrating. 1,2-Diphenylethylene is prepared by reacting benzaldehyde with benzylmagnesium bromide, and then dehydrating. 1,2-Diphenylpropene is also prepared by a similar method. 1,1-Diphenylethylene is prepared by reacting diphenyl ketone with a Grignard reagent such as methylmagnesium iodide, and then dehydrating.

Sources & evidence

ORD record
ord-237e3faa691941a89550a3a3934e5486
Source dataset
uspto-grants-1985_03
Patent number
US04506107

Reaction notes

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