Hydrochloric Acid → HCID 178519581, compound

HRID 2081152Notes

Reaction equation

HRID 2081152 reaction equation
[F:1]/[CH:2]=[CH:3]/[C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]3OCCC[O:17]3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1.O1CCCC1.Cl.C1(C)C=CC=CC=1>O>[F:1]/[CH:2]=[CH:3]/[C@H:4]1[CH2:5][CH2:6][C@H:7]([C:10]2[CH:11]=[CH:12][C:13]([CH:16]=[O:17])=[CH:14][CH:15]=2)[CH2:8][CH2:9]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 8028TetrahydrofuranHCID 178506032HCID 178506032, compound

Product 1

HCID 178519581HCID 178519581, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Trans-1-(E-2-fluoro-1-ethenyl)-4-{4-(1,3-dioxan-2-yl)phenyl}cyclohexane (34 g, 0.12 mol), tetrahydrofurane (130 ml) and 3N-hydrochloric acid (130 ml) were heated under reflux with stirring for 5 hours, followed by cooling the reaction mixture, adding toluene (200 ml) and water (200 ml) to the mixture, washing the resulting toluene solution with water, drying over anhydrous magnesium sulfate and distilling off toluene to obtain the objective substance (25 g, 0.11 mol; E:Z=5:1).

Workup

  1. temperatureunder reflux
  2. temperatureby cooling the reaction mixture
  3. washwashing the resulting toluene solution with water
  4. dry with materialdrying over anhydrous magnesium sulfate
  5. distillationdistilling off toluene
  6. customto obtain the objective substance (25 g, 0.11 mol; E:Z=5:1)

Sources & evidence

ORD record
ord-06626425b70744008944db518768e484
Source dataset
uspto-grants-1993_02
Patent number
US05183587

Reaction notes

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