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

HRID 1110489Notes

Reaction equation

HRID 1110489 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.C(N=CC)(C)(C)C.ClP(=O)(OCC)[O:35][CH2:36][CH3:37]>CCCCCC.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:37][CH:36]=[O:35])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 70324,4'-DimethoxybenzophenoneHCID 7912DiisopropylamineHCID 13139Diethyl chlorophosphateHCID 138901N-Ethylidene-2-methylpropan-2-amine

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

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-tert-butylimine (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. Anal. Calculated for C17H16O3 : C, 76.10; H. 6.01 Found: C, 76.29: H, 6.29.

Workup

  1. customThe compound was prepared

Sources & evidence

ORD record
ord-2b8efcade40e4e5c95e4f1d888c37730
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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