4,4'-Dichlorobenzophenone → 3,3-Bis(4-chlorophenyl)prop-2-enal

HRID 1110491Notes

Reaction equation

HRID 1110491 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.C(NC(C)C)(C)C.C([Li])CCC.ClP(=O)(OCC)[O:31][CH2:32][CH3:33]>CCCCCC.C(N=CC)(C)(C)C.O1CCCC1>[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:33][CH:32]=[O:31])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 70344,4'-DichlorobenzophenoneHCID 7912DiisopropylamineHCID 13139Diethyl chlorophosphateHCID 178418339Butyllithium

Product 1

HCID 145472283,3-Bis(4-chlorophenyl)prop-2-enal

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 138901N-Ethylidene-2-methylpropan-2-amineSolvent

Procedure

The compound was prepared according to the procedure described in Example 84. The following reagents were used: 4,4'-dichlorobenzophenone (25.1 g), diisopropylamine (32.2 mL), 1.6M n-butyl lithium in hexane (144 mL), acetaldehyde N-tert-butylimine (14.75 mL), diethyl chlorophosphonate (16.6 mL) and tetrahydrofurane (200 mL). The usual work up furnished 23.8 g of essentially pure 3,3-bis(4-chlorophenyl)-2-propenal as an orange oil.

Workup

  1. customThe compound was prepared

Sources & evidence

ORD record
ord-2aa2454ba0044cca8dea5d3d7dc50d19
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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