Hydrochloric Acid → (E)-1-(4-Chloro-1-butenyl)-4-fluorobenzene

HRID 1789454Notes

Reaction equation

HRID 1789454 reaction equation
[CH:1]1([CH:4]([C:6]2[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=2)O)[CH2:3][CH2:2]1.[ClH:13]>C(Cl)(Cl)Cl>[Cl:13][CH2:3][CH2:2]/[CH:1]=[CH:4]/[C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 102498alpha-Cyclopropyl-4-fluorobenzenemethanol

Product 1

HCID 20188301(E)-1-(4-Chloro-1-butenyl)-4-fluorobenzene

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Dissolve 12.8 g (0.077 mole) of α-cyclopropyl-4-fluorobenzenemethanol in 60 ml of CHCl3, add 20 ml of concentrated HCl and reflux overnight. Separate the two layers, and extract the aqueous layer with methylene chloride. Combine the methylene chloride extracts with the chloroform layer and wash with saturated aqueous sodium bicarbonate, and dry over magnesium sulfate. Evaporate the organic solvents to yield the title compound.

Workup

  1. temperaturereflux overnight
  2. customSeparate the two layers
  3. extractionextract the aqueous layer with methylene chloride
  4. washwash with saturated aqueous sodium bicarbonate
  5. dry with materialdry over magnesium sulfate
  6. customEvaporate the organic solvents

Sources & evidence

ORD record
ord-e683030b619748749d3b54d0c6f9699e
Source dataset
uspto-grants-1987_08
Patent number
US04689341

Reaction notes

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