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

HRID 1248067Notes

Reaction equation

HRID 1248067 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[OH-].[Na+].[CH3:15][C:16]([CH3:18])=[O:17].Cl>CCCCCCC.C(O)(C)C.O>[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[CH:15][C:16](=[O:17])[CH:18]=[CH:7][C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:11])[F:12])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1

Participants

8

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 679964-(Trifluoromethyl)benzaldehyde

Product 1

HCID 5922411,5-Bis[4-(trifluoromethyl)phenyl]penta-1,4-dien-3-oneYield 79.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 8900HeptaneSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of 4-trifluoromethylbenzaldehyde (64.2 g; 0.369 mol) in heptane (70 ml) is stirred under a nitrogen atmosphere, then sodium hydroxide (15 g; 10% aq), water (30 g), and bis(2-hydroxyethyl)tallowamine N-oxide (6 g) are added. Next a solution of acetone (10.7 g; 0.184 mol) in heptane (30 ml) is added at 25° C. to 35° C. over a period of two hours. The resulting slurry 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 and the mixture heated at reflux for 1.5 hours, and is then cooled to 20° C. The solid is filtered, washed with heptane (40 ml) and water, and is dried to afford 54.5 g of 99.9% pure title product (yield: 79.1%), mp 153° C. to 155° C.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 1.5 hours
  3. filtrationThe solid is filtered
  4. washwashed with heptane (40 ml) and water
  5. customis dried

Sources & evidence

ORD record
ord-f74230ace34a4f6188b8c24d0a9de6e2
Source dataset
uspto-grants-1985_06
Patent number
US04521629

Reaction notes

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