2,2,2-Trifluoroacetophenone → 9-Phenyl-9-trifluoromethyl-2,7-dimethylxanthene

HRID 465734Notes

Reaction equation

HRID 465734 reaction equation
[C:1]1([CH3:15])[CH:6]=[CH:5][C:4]([O:7][C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.[F:16][C:17]([C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=O)([F:19])[F:18]>>[C:22]1([C:20]2([C:17]([F:16])([F:18])[F:19])[C:5]3[CH:6]=[C:1]([CH3:15])[CH:2]=[CH:3][C:4]=3[O:7][C:8]3[C:13]2=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=3)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 99052,2,2-TrifluoroacetophenoneHCID 74098Benzene, 1,1'-oxybis[4-methyl-

Product 1

HCID 151808189-Phenyl-9-trifluoromethyl-2,7-dimethylxanthene

Procedure

The parent monomer (II, Rf =CF3) was prepared (Scheme VI) using the single-bridging process by reaction of p-tolyl ether (X) and trifluoromethylphenyl ketone in HF at 130° C. to provide 9-phenyl-9-trifluoromethyl-2,7-dimethylxanthene (XIX), followed by oxidation to the dicarboxylic acid (XX) and catalytic decarboxylation to (II). The diacid (XX) could also be converted to the diacyl chloride (XXI), then to the diacyl azide and, finally, to the diisocyanate (XXII) as previously described.

Sources & evidence

ORD record
ord-d2b3c047955a40b5ad8a31f78d7bac91
Source dataset
uspto-grants-1992_10
Patent number
US05153336

Reaction notes

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