O-Xylene → HCID 67946614, compound

HRID 1086761Notes

Reaction equation

HRID 1086761 reaction equation
[O:1]([C:8]1([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:13]=[CH:12][CH:11]=[C:10]([OH:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C(C)=CC=CC=1.[OH-].[K+].[F:32][C:33](F)=[C:34]([F:39])[C:35]([F:38])([F:37])[F:36]>O1CCCC1.O>[F:32][C:33]([O:14][C:10]1[CH2:9][C:8]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:13]=[CH:12][CH:11]=1)=[C:34]([F:39])[C:35]([F:38])([F:37])[F:36]

Participants

7

Reactant 4

HCID 7237O-XyleneHCID 8302HexafluoropropyleneHCID 14797Potassium HydroxideHCID 19818095HCID 19818095, compound

Product 1

HCID 67946614HCID 67946614, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Five g (0.018 mole) of 3-phenoxy-3-phenoxyphenol, 100 ml of xylene and 1.2 g of KOH are placed into a flask equipped with a Dean-Stark trap. This mixture is stirred at reflux until water of reaction ceases to evolve. The mixture is cooled and 100 ml of tetrahydrofuran (THF) are added and the mixture is further cooled in a dry ice/acetone bath while 15 g of perfluoropropene are bubbled into the reaction mixture. The mixture is stirred for three hours while warming to room temperature. Next, 100 ml of water are added and the mixture is stirred. The product phase is separated, dried over sodium sulfate, filtered and distilled. The product propene is an oil obtained in a yield of 75 percent. The oil has a pour point below -27° C., a boiling point of 150° C. at 1.0 mm Hg and a DSC of 373° C.

Workup

  1. customequipped with a Dean-Stark trap
  2. temperatureThe mixture is cooled
  3. customare bubbled into the reaction mixture
  4. stirringThe mixture is stirred for three hours
  5. additionNext, 100 ml of water are added
  6. stirringthe mixture is stirred
  7. customThe product phase is separated
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. distillationdistilled
  11. customobtained in a yield of 75 percent
  12. customa pour point below -27° C.
  13. customa DSC of 373° C.

Sources & evidence

ORD record
ord-cb582e5f768d4c83a1e081022d2b1b2e
Source dataset
uspto-grants-1991_07
Patent number
US05032301

Reaction notes

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