Water → Benzene, 1,1'-oxybis[4-methyl-

HRID 262432

Reaction equation

HRID 262432 reaction equation
F[C:2](F)=[C:3](F)F.[K].[CH:8]1[C:13]([OH:14])=[CH:12][CH:11]=[C:10]([CH3:15])[CH:9]=1.O>CN(C)C=O>[C:13]1([O:14][C:8]2[CH:13]=[CH:12][C:2]([CH3:3])=[CH:10][CH:9]=2)[CH:12]=[CH:11][C:10]([CH3:15])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2879P-CresolHCID 8301TetrafluoroethyleneHCID 5462222Potassium

Product 1

HCID 74098Benzene, 1,1'-oxybis[4-methyl-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Tetrafluoroethylene pentamer (50 g) was added dropwise to the potassium salt of p-cresol (15 g) stirred in dry dimethyl formamide (100 ml) at 30° C. After addition of the pentamer, the reaction mixture was stirred for 45 minutes at 60° C. The cooled reaction mixture was poured into water. The oil which separated out was dissolved in ether, the ether layer washed with water, dried over magnesium sulphate, and distilled to give 40 g of the p-cresyl ether, C10F19OC6H4CH3, boiling point 110° C. to 114° C. at 10 mm Hg. Elementary analysis, infra-red spectra, mass spectrometry and nuclear magnetic resonance measurements confirmed the identity of the compound.

Workup

  1. additionAfter addition of the pentamer
  2. customThe cooled reaction mixture
  3. customThe oil which separated out
  4. dissolutionwas dissolved in ether
  5. washthe ether layer washed with water
  6. dry with materialdried over magnesium sulphate
  7. distillationdistilled

Sources & evidence

ORD record
ord-93f1cc33df1c455eb6b768d16eca89f3
Source dataset
uspto-grants-1979_05
Patent number
US04154753

Linked notes

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