1,4-Dioxane → HCID 178516048, compound

HRID 726499Notes

Reaction equation

HRID 726499 reaction equation
C1O[C:4]2([CH2:9][CH2:8][CH:7]([C@H:10]3[CH2:15][CH2:14][C@H:13]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[C:17]=4[F:23])[CH2:12][CH2:11]3)[CH2:6][CH2:5]2)[O:3]C1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O1CCOCC1>O>[F:23][C:17]1[C:18]([F:22])=[CH:19][CH:20]=[CH:21][C:16]=1[C@H:13]1[CH2:12][CH2:11][C@H:10]([CH:7]2[CH2:8][CH2:9][C:4](=[O:3])[CH2:5][CH2:6]2)[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 178505690HCID 178505690, compound

Product 1

HCID 178516048HCID 178516048, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

First, 5.85 g of 4-[trans-4-(2,3-difluorophenyl)cyclohexyl]cyclohexanone ethylene ketal, 0.5 g of p-toluenesulfonic acid monohydrate, 35 ml of dioxane, and 105 ml of water were placed in a 200 ml flask. The mixture was stirred under reflux for 2 hours. The reaction mixture was extracted with ether. The ether layer was washed with water and dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled away. The residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=9/1), distilled under reduced pressure, and recrystallized from hexane to obtain 2.2 g of 4-[trans-4-(2,3-difluorophenyl)cyclohexyl]cyclohexanone (Y: 55.8%). The compound thus obtained had a purity of 98.1% by GC and a b.p. of 165° C./0.5 mmHg.

Workup

  1. temperatureunder reflux for 2 hours
  2. extractionThe reaction mixture was extracted with ether
  3. washThe ether layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThereafter, the solvent was distilled away
  6. customThe residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=9/1)
  7. distillationdistilled under reduced pressure
  8. customrecrystallized from hexane

Sources & evidence

ORD record
ord-836e3c3e164543a5b1374b47c40f28b8
Source dataset
uspto-grants-1998_01
Patent number
US05709911

Reaction notes

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