Acetophenone → 3-(p-Diethylaminophenyl)-1,5-diphenylpentane-1,5-dione

HRID 344815

Reaction equation

[OH-:1].[Na+].[CH2:3]([N:5]([CH2:14][CH3:15])[C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1)[CH3:4].[C:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:18])[CH3:17]>C(O)C>[CH2:3]([N:5]([CH2:14][CH3:15])[C:6]1[CH:13]=[CH:12][C:9]([CH:10]([CH2:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:1])[CH2:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:18])=[CH:8][CH:7]=1)[CH3:4]

Participants

Conditions

Temperature: 50 °C

Procedure

18 g of 50% by weight sodium hydroxide solution were added dropwise to 17.7 g of p-diethylaminobenzaldehyde and 26.4 g of acetophenone in 150 ml of ethanol at 20° C. The mixture was then stirred at 20° C. for 2 hours and at 50° C. for 5 hours. The precipitate was filtered off and washed with ethanol until the residue was only pale yellowish and then with water until neutral. 33.6 g of 3-(p-diethylaminophenyl) -1,5-diphenylpentane-1,5-dione were obtained. The almost colorless crystals melt at 110° C.

Workup

filtrationThe precipitate was filtered off
washwashed with ethanol until the residue

Sources & evidence

ORD record: ord-407808d8942048f7990a431a8151f526
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05053524

Linked notes

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