ChemicalBook CAS DataBase List Cyclopentanecarbaldehyde

Cyclopentanecarbaldehyde synthesis

12synthesis methods

Product Name:Cyclopentanecarbaldehyde
CAS Number:872-53-7
Molecular formula:C6H10O
Molecular Weight:98.14

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Yield:872-53-7 71 %Spectr.

Reaction Conditions:

Stage #1: 6-iodo-1-ethoxyhexyne in hexanes;diethyl ether at -78 - 20; for 2.66667 h;Inert atmosphere;
Stage #2: with methanol in hexanes;diethyl ether at -78 - 20; for 0.5 h;
Stage #3: with perchloric acid in hexanes;diethyl ether at 20; for 18 h;regiospecific reaction;

Steps:

4.8. Hydrolysis of 2a and 2b. Formation of cyclopentane carboxaldehyde

General procedure: A 0.1 M solution of 0.27 mmol iodo ynol ether (2a or 2b) in hexanes-Et₂O was deoxygenated by bubbling N₂ for 5 min. The mixture was cooled to -78 °C. A solution of freshly titrated n-BuLi in hexanes (0.57 mmol) was added dropwise. The solution was stirred for 10 more minutes at -78 °C and then the cooling bath was removed. The reaction mixture was stirred 2 h at room temperature in order for the cyclization to occur. MeOH (6 equiv) was added and the reaction mixture was stirred for another 30 min at room temperature. To this solution were added 1-2 drops of 35% perchloric acid. The reaction mixture was stirred for 18 h at room temperature, diluted with ether, and quenched with 5% NaHCO₃. The ethereal layer was washed with brine, dried over MgSO₄, and concentrated by rotary evaporation with a bath temperature maintained at 0 °C. Comparison of NMR signals of this crude material with the commercially available cyclopentane carboxaldehyde confirmed the structure of cyclopentane carboxaldehyde. The crude mixture revealed a 71% NMR yield starting with 2a and a 77% NMR yield starting with 2b.

References:

Hanna, Rana;Daoust, Benoit [Tetrahedron,2011,vol. 67,# 1,p. 92 - 99] Location in patent:experimental part

2591-86-8 Synthesis