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

HRID 65232
Notes
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Reaction equation

HRID 65232 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-2e3a2ad4ee894bbea0d45c4ba970aa58
Source dataset
uspto-grants-1986_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04613609

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes