2,2,2-Trifluoroacetophenone → HCID 21740023, compound

HRID 2082429Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[CH3:24])[O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([CH3:20])[CH:14]=2)=[CH:8][CH:7]=1.[F:25][C:26]([F:36])([F:35])[C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=O.[OH-].[Na+]>C(Cl)Cl>[CH3:1][C:2]1[C:23]([CH3:24])=[CH:22][C:21]2[C:27]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([C:26]([F:36])([F:35])[F:25])[C:7]3[C:6](=[CH:11][C:10]4[C:27]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)([C:26]([F:35])([F:25])[F:36])[C:18]5[C:13]([O:12][C:9]=4[CH:8]=3)=[CH:14][C:15]([CH3:20])=[C:16]([CH3:19])[CH:17]=5)[O:5][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 45.7 g (0.144 mole) 1,4-bis(3,4 dimethylphenoxy)benzene, 50.0 g (0.288 mole) trifluoroacetylbenzene, and 90 g (4.5 mole) HF was shaken in an autoclave at 120° C. for 8 hours. The clave contents were transferred to a polyethylene jar, half filled with ice-water, and containing 250 ml 50% NaOH. Methylene chloride was added, the slurry was filtered through Celite®, the organic layer was separated and the extracts were stripped. The residue was stirred with acetone and filtered, yielding 19.4 g of white solid. Because of its low solubility in methylene chloride, some product was lost on the Celite® pad. The IR was sharp, and the NMR was consistent with structure: m 7.33-7.45, 2 s 6.85, 2 s 6.67, s 6.55, 2 s 2.21, s 2.07 ppm in 5:1:1:1:3:3 ratio, indicating presence of cis-trans isomers. Analysis: calc. for C38H28F6O2 : C 72.4; H 4.44; found: C 71.3; H 4.57%.

Workup

filtrationthe slurry was filtered through Celite®
customthe organic layer was separated
stirringThe residue was stirred with acetone
filtrationfiltered

Sources & evidence

ORD record: ord-6b4508d0dcf141b4884a8c391dd3641a
Source dataset: uspto-grants-1993_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05189138

Reaction notes

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