ChemicalBook CAS DataBase List Acetylferrocene

Acetylferrocene synthesis

9synthesis methods

Product Name:Acetylferrocene
CAS Number:1271-55-2
Molecular formula:C12H12FeO10*
Molecular Weight:228.07

Acetylferrocene synthesis: Charge a 25 mL round bottom flask with ferrocene (1 g) and acetic anhydride (3.3 mL). Carefully add phosphoric acid (0.7 mL, 85%) and heat the reaction mixture on a hot water bath for 20 min with stirring. Pour the hot mixture onto crushed ice (27 g). After all the ice has melted, neutralise the solution with solid sodium bicarbonate and cool for a further 5 min. Collect the brown precipitate by filtration, wash with water and dry in the air. The solid obtained is a mixture of unreacted ferrocene and the monosubstituted product acetylferrocene (Figure 1). However, a third compound may also be present in very small amounts as the disubstituted product of acetylation (1,1′-diacetylferrocene).
Preparation of acetylferrocene

1271-47-2 Synthesis

1271-47-2
131 suppliers
$12.00/250mg

7732-18-5
549 suppliers
$12.69/100ml

1271-55-2
223 suppliers
$8.00/1g

Yield:1271-55-2 83%

Reaction Conditions:

in methanol at 150; under 8250.83 Torr; for 14 h;Autoclave;Inert atmosphere;Green chemistry;

Steps:

The general procedure of the reaction
General procedure: In a 100 mL capacity of autoclave vessel a 60 mL solution of methanol and water (1:2) was added, further 1 mmol alkynes were added to this solution. The autoclave was three times purged withthe gas and then nally pressurized up to the 11 bar pressure. The reaction mixture was vigorously stirred at 150 °C for continuous 14 h. After the completion of the reaction, the reactor was cooled to room temperature, and then the argon pressure was carefully released to the atmospheric pressure. Methanol from the reaction mixture is removed using rotatory evaporator. After that, the reaction mixture was transferred in a separating funnel, and it wasworked up with ethyl acetate. The organic layer was separatedand dried over Na2SO4. Afterwards, it was filtered and concentrated under reduced pressure. The resulted crude mixture waspuried by silica gel column chromatography using ethyl acetate/n-hexane as eluent, and pure keto product was isolated.

References:

Ali, Munsaf;Srivastava, Avinash K.;Joshi, Raj K. [Tetrahedron Letters,2018,vol. 59,# 21,p. 2075 - 2078]

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102-54-5 Synthesis