Acetone → 1,5-Bis[4-(trifluoromethyl)phenyl]penta-1,4-dien-3-one

HRID 1248068Notes

Reaction equation

[OH-].[Na+].[F:3][C:4]([F:14])([F:13])[C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1.[CH3:15][C:16]([CH3:18])=[O:17].Cl>CCCCCCC.C(O)(C)C>[F:3][C:4]([F:14])([F:13])[C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH:15][C:16](=[O:17])[CH:18]=[CH:9][C:8]2[CH:7]=[CH:6][C:5]([C:4]([F:3])([F:13])[F:14])=[CH:12][CH:11]=2)=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of sodium hydroxide (15 g of 10% aqueous) is added with stirring, and under a nitrogen atmosphere to a solution of 4-trifluoromethylbenzaldehyde (6.42 g; 0.369 mol) in heptane (70 ml). Next, a solution of acetone (10.7 g; 0.184 mol) in heptane (30 ml) is added to the above two phase system at a temperature range of from 25° C. to 30° C. over a period of two hours. The reaction mixture is then stirred for two hours at 25° C. to 30° C. Concentrated hydrochloric acid (9.4 ml) and isopropyl alcohol (48 ml) are then added, the mixture heated at reflux for 1.5 hours, and is then cooled to 20° C. The precipitated solid is filtered, washed with heptane (40 ml), and water and dried under vacuum to afford 50.8 g of title product, 98.8% pure, mp 154° C. to 156° C. (yield: 73.7%).

Workup

stirringThe reaction mixture is then stirred for two hours at 25° C. to 30° C
temperaturethe mixture heated
temperatureat reflux for 1.5 hours
filtrationThe precipitated solid is filtered
washwashed with heptane (40 ml), and water
customdried under vacuum

Sources & evidence

ORD record: ord-2312fb2aa5914a529f67b9146ca10b3b
Source dataset: uspto-grants-1985_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04521629

Reaction notes

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