Hydrochloric Acid → 1,5-Bis[4-(trifluoromethyl)phenyl]penta-1,4-dien-3-one
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-:13].[Na+].[Cl-].OCC[NH+](CCO)CCCCCCCC/C=[CH:29]\[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38].Cl>CCCCCCC.C(O)(C)C.CC(C)=O.O>[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[CH:38][C:37](=[O:13])[CH:36]=[CH:35][C:34]2[CH:29]=[CH:30][C:31]([C:2]([F:12])([F:11])[F:1])=[CH:32][CH:33]=2)=[CH:5][CH:4]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 40 °C
Procedure
A mixture of 4-trifluoromethylbenzaldehyde (65.2 g; 0.369 mol), heptane (70 ml), 10% sodium hydroxide solution (15 g) and water (30 ml) is stirred under a nitrogen atmosphere and heated to 40° C. Next, a solution of acetone (10.7 g) and of bis(2-hydroxyethyl)methyloleylammonium chloride (1.6 g) in heptane (30 ml) is added dropwise over three hours at the above temperature. After the addition is completed, the mixture is stirred at 40° C. to 45° C. for two hours. After two hours, isopropyl alcohol (68 ml) and hydrochloric acid (9.4 ml; concentrated) are added and the mixture heated at reflux for 1.5 hours. The reaction mixture is then cooled to 20° C., the precipitated solid is isolated by filtration, washed with heptane (40 ml) and water to afford 56.8 g of 99.6% pure title product, mp 154° C. to 156° C. (83.0% yield).
Workup
- additionAfter the addition
- stirringthe mixture is stirred at 40° C. to 45° C. for two hours
- temperaturethe mixture heated
- temperatureat reflux for 1.5 hours
- temperatureThe reaction mixture is then cooled to 20° C.
- customthe precipitated solid is isolated by filtration
- washwashed with heptane (40 ml) and water
Sources & evidence
- ORD record
- ord-d9a2563ecb8642de8499abd3e7420b05
- Source dataset
- uspto-grants-1985_06
- Patent number
- US04521629
Reaction notes
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