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

HRID 729111Notes

Reaction equation

HRID 729111 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-cc196ea0b3da4e3695fe5ca370695b21
Source dataset
uspto-grants-1991_09
Patent number
US05051520

Reaction notes

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