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

HRID 1248069Notes

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.[CH3:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[OH-:20].[Na+].P(=O)(O)(O)O>[Cl-].C[NH2+]CCCCCCCC/C=C\CCCCCCCC(CCO)CCO.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:13][C:14](=[O:20])[CH:15]=[CH:16][C:17]2[CH:5]=[CH:4][C:3]([C:2]([F:12])([F:11])[F:1])=[CH:19][CH:18]=2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 42 °C

Procedure

A mixture of 4-trifluoromethylbenzaldehyde (8.4 kg), heptane (12.1 L), water (5.23 L), 50% sodium hydroxide (0.384 kg) and methyl bis(hydroxyethyl)oleylammonium chloride (0.213 kg) is stirred under a nitrogen atmosphere and heated to 40° C. to 45° C. Acetone (1.44 kg) is added to the above mixture over 2.3 hours. The resulting slurry is stirred and heated at 42° C. for two hours and then 85% phosphoric acid (1.36 kg) is added followed by isopropyl alcohol (8.97 L). The resultant mixture is heated at reflux (73° C.) for 1.5 hours and then cooled to 14° C. The reaction mixture is filtered, the isolated solids washed with heptane (5.29 L) and water (7.12 L). Drying affords 7.2 kg of the title compound, mp 154° C. to 155.5° C.

Workup

temperatureheated to 40° C. to 45° C
stirringThe resulting slurry is stirred
temperatureat reflux (73° C.) for 1.5 hours
temperaturecooled to 14° C
filtrationThe reaction mixture is filtered
washthe isolated solids washed with heptane (5.29 L) and water (7.12 L)
customDrying

Sources & evidence

ORD record: ord-b37ff098eef5425e850927992492df57
Source dataset: uspto-grants-1985_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04521629

Reaction notes

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