Hydrochloric Acid → HCID 178447998, compound

HRID 54040Notes

Reaction equation

HRID 54040 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[F:20])=[C:9](/[C@H:11]2[CH2:16][CH2:15][C@H:14]([CH2:17][CH2:18][CH3:19])[CH2:13][CH2:12]2)\[F:10])=[CH:4][CH:3]=1.Cl.[CH2:22]1[CH2:26]OC[CH2:23]1>>[CH2:23]([C@H:2]1[CH2:7][CH2:6][C@H:5](/[C:8](/[F:20])=[C:9](/[C@H:11]2[CH2:16][CH2:15][C@H:14]([CH2:17][CH2:18][CH3:19])[CH2:13][CH2:12]2)\[F:10])[CH2:4][CH2:3]1)[CH2:22][CH3:26]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 178447996HCID 178447996, compound

Product 1

HCID 178447998HCID 178447998, compoundYield 60%

Conditions

Temperature
-10 °C

Procedure

Then, a mixed solution containing 1.3 g (6.31 mmol) of 2-(trans-4-n-propylcyclohexyl)-1,1,2-trifluoroethylene obtained in Example 1 and 10 ml of dry THF, was dropwise added thereto at the same temperature over a period of 15 minutes. The mixture was reacted at the same temperature for one hour and then the temperature was raised to -10° C. Then, 100 ml of 1N hydrochloric acid was added thereto. The organic layer was separated. The aqueous layer was extracted with n-hexane, and the extract was combined with the organic layer. The combined organic layer was washed with water and dried. Then, the solvent was distilled off, and the obtained crude solution was purified by silica gel column chromatography. The obtained solid was further recrystallized from ethanol to obtain 1.18 g (yield: 60%) of (E)-1,2-bis(trans-4-n-propylcyclohexyl)-1,2-difluoroethylene.

Workup

  1. additionwas dropwise added
  2. customThe mixture was reacted at the same temperature for one hour
  3. customThe organic layer was separated
  4. extractionThe aqueous layer was extracted with n-hexane
  5. washThe combined organic layer was washed with water
  6. customdried
  7. distillationThen, the solvent was distilled off
  8. customthe obtained crude solution
  9. customwas purified by silica gel column chromatography
  10. customThe obtained solid was further recrystallized from ethanol

Sources & evidence

ORD record
ord-1564235662c9419a825d50edec702130
Source dataset
uspto-grants-1997_04
Patent number
US05621147

Reaction notes

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