Aluminum(III) Chloride → HCID 178519740, compound

HRID 259587Notes

Reaction equation

HRID 259587 reaction equation
[C-:1]1([C:6]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]([Cl:14])=O)=[O:7])[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH-:15]1[CH:19]=[CH:18][CH:17]=[CH:16]1.[Fe+2:20].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[Cl:14][C:12]1[CH2:11][CH2:10][CH2:9][C:8]=1[C:6]([C-:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1)=[O:7].[CH-:15]1[CH:19]=[CH:18][CH:17]=[CH:16]1.[Fe+2:20]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 178521142HCID 178521142, compound

Product 1

HCID 178519740HCID 178519740, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This brown oil (ferrocenoyl valeroyl chloride) assumed to be 0.01 mole from the above preparation in methylene chloride (100 ml) was stirred at 0°-5° and aluminium chloride (1.3g; 0.01 mole) was added. Ice was then added and the organic layer was separated. The aqueous layer was extracted with chloroform. The combined organic fractions were washed with water, dried (magnesium sulphate) and evaporated to yield a red oil which was purified by dry-column chromatography on silica, which had been deactivated to Grade III by the addition of water, using 1:10 ethylacetate: petroleum ether as eluent, to yield pure 1-chloro-2-ferrocenoylcyclopent-1-ene, 150 mg; mp 102°.

Workup

  1. additionIce was then added
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted with chloroform
  4. washThe combined organic fractions were washed with water
  5. dry with materialdried (magnesium sulphate)
  6. customevaporated
  7. customto yield a red oil which
  8. customwas purified by dry-column chromatography on silica, which
  9. additionhad been deactivated to Grade III by the addition of water

Sources & evidence

ORD record
ord-6aa19527fd26497393d90c8baf6664d1
Source dataset
uspto-grants-1977_07
Patent number
US04038413

Reaction notes

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