Water → HCID 178519271, compound

HRID 259580Notes

Reaction equation

HRID 259580 reaction equation
[O:1]=[C:2]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:3][CH2:4][CH2:5][CH2:6][C:7](Cl)=O.[CH-:16]1[CH:20]=[CH:19][CH:18]=[CH:17]1.[CH-:21]1[CH:25]=[CH:24][CH:23]=[CH:22]1.[Fe+2:26].[Cl-].[Al+3].[Cl-].[Cl-].O>C(Cl)Cl.C1CCCCC1>[C:2]([C:3]1[CH2:4][CH2:5][CH2:6][C:7]=1[C-:16]1[CH:20]=[CH:19][CH:18]=[CH:17]1)(=[O:1])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH-:21]1[CH:25]=[CH:24][CH:23]=[CH:22]1.[Fe+2:26]

Participants

7

Reactant 4

HCID 962WaterHCID 7611Bis(eta-cyclopentadienyl) ironHCID 6451240Aluminum(III) Chloride2×HCID 12692057HCID 12692057, compound

Product 1

HCID 178519271HCID 178519271, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8078CyclohexaneSolvent

Procedure

6-Oxo-6-phenylhexanoyl chloride (9.0g; 0.04 mole) and ferrocene (7.44g; 0.04 mole) in methylene chloride (150 ml) were stirred at 0° and aluminium chloride (5.34g; 0.04 mole) was added over 40 minutes at 0°. The mixture was stirred at 0° (2 hr), and then at room temperature (90 min). More aluminium chloride (4g; 0.03 mole) was added and the reaction mixture was heated under reflux for 90 minutes. Water was added, the organic layer run off, and the aqueous layer extracted with methylene chloride (100 ml). The combined organic layers were washed with water (3 × 200 ml), and dried (sodium sulphate) to yield a brown oil. The portion of this oil which was insoluble in hot cyclohexane was discarded and the remainder (2.7g) was subjected to preparative thin layer chromatography to yield 2.1g (15%) of pure 1-benzoyl-2-ferrocenylcyclopentene as a brown solid mp 136°-137°.

Workup

  1. customat room temperature
  2. custom(90 min)
  3. temperaturethe reaction mixture was heated
  4. temperatureunder reflux for 90 minutes
  5. extractionthe organic layer run off, and the aqueous layer extracted with methylene chloride (100 ml)
  6. washThe combined organic layers were washed with water (3 × 200 ml)
  7. dry with materialdried (sodium sulphate)
  8. customto yield a brown oil

Sources & evidence

ORD record
ord-005b6f4915974515ac80fd7cdb910300
Source dataset
uspto-grants-1977_07
Patent number
US04038413

Reaction notes

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