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

HRID 1590329Notes

Reaction equation

HRID 1590329 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-0a5b56b15120418d99bb26ef059709f2
Source dataset
uspto-grants-1993_04
Patent number
US05202446

Reaction notes

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