Benzaldehyde → 1,1-Diphenylethylene

HRID 2412807Notes

Reaction equation

HRID 2412807 reaction equation
[BH4-].[Na+].[C:3]1([CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2C=O)[CH3:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C[Mg]I.[CH:22](=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[CH2:30]([Mg]Br)C1C=CC=CC=1.[C:39]1([CH:45]=[C:46]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)C)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C1(C(C2C=CC=CC=2)=O)C=CC=CC=1>>[C:23]1([CH:22]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[C:9]([CH3:11])=[CH2:10])[CH3:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[C:39]1([CH:45]=[CH:46][C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.[C:3]1([C:9]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH2:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

10

Reactant 7

HCID 240BenzaldehydeHCID 3102BenzophenoneHCID 130701,2-Diphenyl-1-propeneHCID 4311764Sodium borohydrideHCID 125353482-(1-Phenylethyl)benzaldehydeHCID 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(formylphenyl)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-63d840fcdc7c4fffacb02ca464cedc3f
Source dataset
uspto-grants-1985_01
Patent number
US04493943

Reaction notes

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