Ethanol → 4-Dimethylamino-2',3',4'-trimethoxychalcone

HRID 1200196Notes

Reaction equation

[OH-:1].[Na+].[CH3:3][O:4][C:5](OC)(OC)[C:6]([C:8]1[CH:13]=C[CH:11]=[CH:10][CH:9]=1)=[O:7].[CH3:18][N:19]([C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1C=O)[CH3:20].[CH2:29](O)C.[C:32]([O:35][CH2:36][CH3:37])(=O)C>CCCCCC>[CH3:20][N:19]([CH3:18])[C:21]1[CH:22]=[CH:25][C:26]([CH:11]=[CH:10][C:9]([C:8]2[CH:13]=[CH:37][C:36]([O:35][CH3:32])=[C:5]([O:4][CH3:3])[C:6]=2[O:7][CH3:29])=[O:1])=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydroxide (0.5 ml of 2N) was added to a mixture of trimethoxyacetophenone (2.1 g, 0.01 mole), dimethylaminobenzaldehyde (1.49 g, 0.01 mole), and ethanol (50 ml). The reaction mixture was allowed to stir at room temperature until a thin layer chromatography (50% ethyl acetate in hexane) indicated that the reaction was complete. After cooling to about 0° C., the mixture was filtered, the solid residue washed with water, then with methanol. Recrystallization from methanol gave the title compound, m.p. 145°-146° C. Elemetal analysis for C20H23NO4 : Calcd: C, 70.36; H, 6.79; N, 4.10%. Found: C, 70.21; H, 6.98; N, 3.83%. Also prepared by substantially the same procedure as in example 2 were:

Workup

filtrationthe mixture was filtered
washthe solid residue washed with water
customRecrystallization from methanol

Sources & evidence

ORD record: ord-1699ec48951241ebacd126590d6764f8
Source dataset: uspto-grants-1990_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04904697

Reaction notes

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