4,4'-Dichlorobenzophenone → (E)-5,5-bis(4-chlorophenyl)-2,4-pentadienoic acid ethyl ester

HRID 1886547Notes

Reaction equation

HRID 1886547 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)=O)=[CH:4][CH:3]=1.[CH3:17][CH2:18][O:19][C:20](/[CH:22]=[CH:23]/[CH2:24]P(OCC)(OCC)=O)=[O:21].[H-].[Na+]>>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)=[CH:24]/[CH:23]=[CH:22]/[C:20]([O:19][CH2:18][CH3:17])=[O:21])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 70344,4'-DichlorobenzophenoneHCID 24758Sodium hydrideHCID 5365783Triethyl 4-phosphonocrotonate, mixture of isomers

Product 1

HCID 14347256(E)-5,5-bis(4-chlorophenyl)-2,4-pentadienoic acid ethyl esterYield 28.1%

Procedure

By the method of Preparation 1, 4,4'-dichlorobenzophenone (5.00 g, 19.9 mmol) was hologated using triethyl 4-phosphonocrotonate (5.23 g, 20.9 mmol) and sodium hydride (0.528 g, 22 mmol) to give, after purification, 1.94 g (28% yield) of title product, mp 99-100° C.

Workup

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Sources & evidence

ORD record
ord-410908bc4aef4e039d767d523c529bd2
Source dataset
uspto-grants-1992_09
Patent number
US05151545

Reaction notes

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