Water → HCID 178520610, compound

HRID 259583Notes

Reaction equation

HRID 259583 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([CH2:8][CH2:9][CH2:10][CH2:11][C:12](Cl)=[O:13])=[O:7])=[CH:4][CH:3]=1.[CH-:17]1[CH:21]=[CH:20][CH:19]=[CH:18]1.[CH-:22]1[CH:26]=[CH:25][CH:24]=[CH:23]1.[Fe+2:27].[Cl-].[Al+3].[Cl-].[Cl-].O>C(Cl)Cl>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]([C-:17]2[CH:21]=[CH:20][CH:19]=[CH:18]2)=[O:13])=[O:7])=[CH:4][CH:3]=1.[CH-:22]1[CH:26]=[CH:25][CH:24]=[CH:23]1.[Fe+2:27]

Participants

6

Reactant 4

HCID 962WaterHCID 7611Bis(eta-cyclopentadienyl) ironHCID 6451240Aluminum(III) ChlorideHCID 135988994-Chloro-ε-oxobenzenehexanoyl chloride

Product 1

HCID 178520610HCID 178520610, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(4-Chlorobenzoyl)pentanoyl chloride (5.2g; 0.02 mole) in methylene chloride (100 ml) and ferrocene (3.75g; 0.02 mole) were stirred at 0.5° and aluminium chloride (2.7g; 0.02 mole) was added slowly over 0.5 hr. The mixture was stirred at 0.5° for 1.5 hr then water was added. The organic layer was separated. The aqueous layer was extracted with methylene chloride and the combined organic fractions were washed with water, dried (magnesium sulphate) and evaporated to yield a brown solid. This was recrystallized from petroleum ether (60°-80°) to yield pure 5-(4-chlorobenzoyl)pentanoyl ferrocene; 3.23g (40%); mp 103°-106°.

Workup

  1. customThe organic layer was separated
  2. extractionThe aqueous layer was extracted with methylene chloride
  3. washthe combined organic fractions were washed with water
  4. dry with materialdried (magnesium sulphate)
  5. customevaporated
  6. customto yield a brown solid
  7. customThis was recrystallized from petroleum ether (60°-80°)

Sources & evidence

ORD record
ord-7257da434d7f4ae09948035558a99c5e
Source dataset
uspto-grants-1977_07
Patent number
US04038413

Reaction notes

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