Water → HCID 178520610, compound

HRID 1657505Notes

Reaction equation

HRID 1657505 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°-6°.

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-3ddcaf88a25f497dbdad26422e636aab
Source dataset
uspto-grants-1976_06
Patent number
US03960911

Reaction notes

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