Cyclohexanone → HCID 18959824, compound
Reaction equation
[C:1]1([Mg]Br)[CH:6]=[C:5]([CH3:7])[CH:4]=[CH:3][C:2]=1[CH3:8].[C:11]1(=O)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.BrC1CCCC=C1>>[C:1]1([C:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=2)[CH:6]=[C:5]([CH3:7])[CH:4]=[CH:3][C:2]=1[CH3:8]Participants
4
Procedure
Phenylterephthalic acid is valuable as an interemediate in the preparation of liquid crystalline polyesters. For example, U.S. Pat. No. 4,391,966 describes the use of phenylterephthalic acid in preparing melt-spinnable, anisotropic melt forming aromatic polyesters. Further, E. K. Weisburger and J. H. Weisburger describe the reaction of 2,5-xylylmagnesium bromide with either cyclohexanone or 3-bromocyclohexene to provide 1-(2,5-xylyl)cyclohexene, which is then dehydrogenated using sulfur to provide 2,5-dimethylbiphenyl, which is oxidized by KMnO4 to provide phenylterephthalic acid in 74% yield. The permangenate process provides an isolation and purification problem, since a relatively large amount of manganese waste is produced.
Sources & evidence
- ORD record
- ord-e8c0961a137a42d9915cdc4a0e3e5234
- Source dataset
- uspto-grants-1994_10
- Patent number
- US05359134
Reaction notes
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