Water → 3-Benzoyl-2-ferrocenylcyclohexene

HRID 1657507Notes

Reaction equation

HRID 1657507 reaction equation
[O:1]=[C:2]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]([C-:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1)=O.[CH-:21]1[CH:25]=[CH:24][CH:23]=[CH:22]1.[Fe+2:26].O>OS(O)(=O)=O.C(O)(=O)C>[C:2]([CH:3]1[CH2:4][CH2:5][CH2:6][CH:7]=[C:8]1[C-:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1)(=[O:1])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH-:21]1[CH:25]=[CH:24][CH:23]=[CH:22]1.[Fe+2:26]

Participants

4

Reactant 2

HCID 962WaterHCID 178520604HCID 178520604, compound

Product 1

HCID 1317102803-Benzoyl-2-ferrocenylcyclohexeneYield 36.2%

Reagents, catalysts & solvents 1

HCID 23350293Acetic acid sulfuric acidSolvent

Procedure

7-Oxo-7-phenylheptanoylferrocene (1.94g; 5 mmole) was dissolved in 5% H2SO4 /acetic acid (40 ml; excess) at room temperature. The solution was stirred overnight and then poured into water (400 ml) and extracted with chloroform (3 × 200 ml). The organic layers were extracted with water, saturated aqueous sodium bicarbonate, and water, and dried (Na2SO4) to yield a brown oil. The crude product was suspended in hot petroleum ether (bp 40°-60°C) and filtered. The filtrate was submitted to preparative thin layer chromatography on silica. The main yellow band was eluted with petroleum ether/ethyl acetate (10:1) and gave 670 mg (36.2%) of pure 3-benzoyl-2-ferrocenylcyclohexene mp 127°-9°C.

Workup

  1. extractionextracted with chloroform (3 × 200 ml)
  2. extractionThe organic layers were extracted with water, saturated aqueous sodium bicarbonate, and water
  3. dry with materialdried (Na2SO4)
  4. customto yield a brown oil
  5. filtrationfiltered
  6. washThe main yellow band was eluted with petroleum ether/ethyl acetate (10:1)

Sources & evidence

ORD record
ord-2596e15aa227448f9d80dfc87c7393aa
Source dataset
uspto-grants-1976_06
Patent number
US03960911

Reaction notes

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