Water → HCID 178519273, compound

HRID 259584Notes

Reaction equation

HRID 259584 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]([C-:14]2[CH:18]=[CH:17][CH:16]=[CH:15]2)=O)=[O:7])=[CH:4][CH:3]=1.[CH-:21]1[CH:25]=[CH:24][CH:23]=[CH:22]1.[Fe+2:26].S(=O)(=O)(O)O.O>C(O)(=O)C>[C-:14]1([C:12]2[CH2:11][CH2:10][CH2:9][C:8]=2[C:6](=[O:7])[C:5]2[CH:19]=[CH:20][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH:18]=[CH:17][CH:16]=[CH:15]1.[CH-:21]1[CH:25]=[CH:24][CH:23]=[CH:22]1.[Fe+2:26]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 178520610HCID 178520610, compound

Product 1

HCID 178519273HCID 178519273, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-(4-Chlorobenzoyl)pentanoyl ferrocene (8.2g; 0.02 mole) and 5% (v/v) concentrated sulphuric acid in glacial acetic acid (200 ml) were stirred at room temperature for 1 hour, the mixture was poured into water and extracted with chloroform (3 × 100 mls.). The combined extracts were washed with saturated aqueous sodium bicarbonate, and water, dried (magnesium sulphate) and evaporated under vacuum to yield a red-brown oil which crystallized from pentane at 0°-5°. The solid was filtered off to yield pure 1-ferrocenyl-2-(4-chlorobenzoyl)cyclopent-1-ene; 2.5g (35%) mp 121°-123°.

Workup

  1. extractionextracted with chloroform (3 × 100 mls.)
  2. washThe combined extracts were washed with saturated aqueous sodium bicarbonate, and water
  3. dry with materialdried (magnesium sulphate)
  4. customevaporated under vacuum
  5. customto yield a red-brown oil which
  6. customcrystallized from pentane at 0°-5°
  7. filtrationThe solid was filtered off

Sources & evidence

ORD record
ord-fad2bf787b664a1b99a6a81f17c46ac3
Source dataset
uspto-grants-1977_07
Patent number
US04038413

Reaction notes

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