1-Indanone → 1H-Inden-1-one, 2-[[4-(diethylamino)-2-methylphenyl]methylene]-2,3-dihydro-

HRID 971939Notes

Reaction equation

[C:1]1(=[O:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[CH2:11]([N:13]([CH2:23][CH3:24])[C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[C:16]([CH3:22])[CH:15]=1)[CH3:12].[OH-].[Na+]>C(O)C>[CH2:23]([N:13]([CH2:11][CH3:12])[C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[C:2]2[CH2:3][C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:1]2=[O:10])=[C:16]([CH3:22])[CH:15]=1)[CH3:24]

Participants

Conditions

Temperature: 5 °C

Procedure

A solution of 50 g. (0.3785 mole) 1-indanone and 77.75 g. of 93% 4-diethylamino-2-methylbenzaldehyde in 150 ml. of ethanol was stirred and 94 ml. of a solution of warm (approx. 30° C.) 25% aqueous sodium hydroxide was added. This reaction mixture was heated to reflux for 45 minutes. A solid precipitate began appearing after 30 minutes. Next, the mixture was cooled to about 5° C. and the precipitate filtered and washed with petroleum ether. After air drying, the resulting solid was washed with water until the wash material was pH 7.0. The washed precipitate was recrystallized from 80% aqueous ethanol to yield 92.6 g. (80.1% yield) of 2-(4'-diethylamino-2'-methylbenzylidene)-1-indanone (m.p. 133.5°-134.5° C.), U.V. spectra and ε values are set forth in Table 3 below. The structure was confirmed by both infrared and nuclear magnetic resonance spectra.

Workup

additionwas added
temperatureThis reaction mixture was heated
temperatureto reflux for 45 minutes
filtrationthe precipitate filtered
washwashed with petroleum ether
customAfter air drying
washthe resulting solid was washed with water until the wash material
customThe washed precipitate was recrystallized from 80% aqueous ethanol
customto yield 92.6 g

Sources & evidence

ORD record: ord-4b336c75c7b24f33ad01e7c3128a6d5e
Source dataset: uspto-grants-1979_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04162162

Reaction notes

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