Hydrochloric Acid → HCID 71087315, compound

HRID 2045737Notes

Reaction equation

HRID 2045737 reaction equation
C(C1C=CC(C2C=CC(C(C)(C)C)=CC=2)=CC=1)(C)(C)C.[Li].Cl[CH2:23][CH:24]1[CH2:29][CH2:28][CH:27]([CH:30]2[CH2:35][CH2:34][CH:33]([CH2:36][CH2:37][CH3:38])[CH2:32][CH2:31]2)[CH2:26][CH2:25]1.[F:39][C:40]([F:44])=[C:41](F)[F:42].Cl>C1(C)C=CC=CC=1.C1COCC1>[CH2:36]([CH:33]1[CH2:34][CH2:35][CH:30]([CH:27]2[CH2:26][CH2:25][CH:24]([CH2:23][C:41]([F:42])=[C:40]([F:44])[F:39])[CH2:29][CH2:28]2)[CH2:31][CH2:32]1)[CH2:37][CH3:38]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8301TetrafluoroethyleneHCID 741954,4'-Bis(1,1-dimethylethyl)-1,1'-biphenylHCID 3028194LithiumHCID 13608779HCID 13608779, compound

Product 1

HCID 71087315HCID 71087315, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a reaction vessel under an argon atmosphere, 41.5 g of 4,4′-di-t-butyl-biphenyl and 500 ml of THF were added, and the resultant solution was cooled to 0° C. Thereto, 2.16 g of metal lithium was added a little at a time, and stirring was carried out for 3 hours. Next, a THF 100 ml solution of 20.0 g of 4-chloromethyl-4′-propylbicyclohexane was slowly added dropwise, and stirring was carried out for another 3 hours. Then 9.00 g of tetrafluoroethylene was added to allow reaction for 30 minutes while returning to room temperature. The resultant reaction mixture was poured into 500 ml of 1N hydrochloric acid, and mixing was carried out. Then, 500 ml of toluene was added to separate layers to an organic layer and an aqueous layer, and an extraction operation was performed. The resultant organic layer was sequentially washed with 1N hydrochloric acid and water, and the resultant solution was dried over anhydrous magnesium sulfate. The resultant solution was concentrated under reduced pressure, a residue was purified by fractionation by means of column chromatography (silica gel; heptane), and thus 21.9 g of 4-propyl-4′-(2,3,3-trifluoroallyl)-1,1′-bicyclohexane (T-2) was obtained. Yield from compound (T-1) was 93%.

Workup

  1. stirringstirring
  2. waitwas carried out for another 3 hours
  3. customreaction for 30 minutes
  4. customwhile returning to room temperature
  5. customThe resultant reaction mixture
  6. additionmixing
  7. customto separate layers to an organic layer
  8. washThe resultant organic layer was sequentially washed with 1N hydrochloric acid and water
  9. dry with materialthe resultant solution was dried over anhydrous magnesium sulfate
  10. concentrationThe resultant solution was concentrated under reduced pressure
  11. customa residue was purified by fractionation by means of column chromatography (silica gel; heptane)

Sources & evidence

ORD record
ord-aac5f162bded460b8b7188525a24ff78
Source dataset
uspto-grants-2013_11
Patent number
US08592008B2

Reaction notes

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