4,4'-Dimethoxybenzophenone → 3,3-bis(4-Methoxyphenyl)-2-propenal

HRID 2232735Notes

Reaction equation

HRID 2232735 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=O)=[CH:5][CH:4]=1.C(NC(C)C)(C)C.ClP(=O)(OCC)[O:28][CH2:29][CH3:30]>CCCCCC.C(N=CC)(C)(C)C.O1CCCC1>[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[CH:30][CH:29]=[O:28])=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 70324,4'-DimethoxybenzophenoneHCID 7912DiisopropylamineHCID 13139Diethyl chlorophosphate

Product 1

HCID 141685443,3-bis(4-Methoxyphenyl)-2-propenal

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 except that the reaction time was extended to 68 hours. The following reagents were used: 4,4'-dimethoxybenzophenone (24.2 g), diisopropylamine (32.2 mL) 1.55M n-butyl lithium in hexane (148 mL), acetaldehyde N-tertbutylimine (14.75 mL), diethyl chlorophosphonate (16.6 mL) and tetrahydrofurane (200 mL). The usual work up furnished 25.6 g of an orange oil which was crystallized from ether-hexane to give 22.7 g of 3,3-bis(4-dimethoxyphenyl)-2-propenal, as a yellow solid, mp 55°-57° C. The analytical specimen, mp 56°-57° C. Crystallized from the same solvent system, had been prepared in a previous experiment.

Workup

  1. customThe compound was prepared

Sources & evidence

ORD record
ord-05bdcee0eaf047bda46bc2810f9e6dec
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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