Cyclohexylideneacetaldehyde synthesis
- Product Name:Cyclohexylideneacetaldehyde
- CAS Number:1713-63-9
- Molecular formula:C8H12O
- Molecular Weight:124.18
6975-71-9
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Yield:1713-63-9 81 %Chromat.
Reaction Conditions:
with 1,1,3,3-Tetramethyldisiloxane;vanadium(V) oxytriisopropoxide in toluene at 60; for 20 h;
Steps:
General procedure for the reduction of nitriles into aldehydes:
General procedure: 40-Methyl-2-biphenylcarbonitrile 1d (Table 2 entry 4). To a nitrogen purged screw-capedvial containing 1d (630 mg, 3.3 mmol, 1.0 equiv) in 500 lL of toluene wereadded TMDS (5.8 mL, 32.8 mmol, 10.0 equiv) and V(O)(OiPr)3 (780 lL,3.3 mmol, 1.0 equiv) at rt. The mixture was then heated at 60 C for 20 h(the colorless solution turned into deep purple) and then cooled to roomtemperature. The clear solution was diluted with toluene (10 mL) and acidifiedusing aqueous H3PO4 85% (2.0 g diluted in 5.0 ml of water, 5.2 equiv). Theorganic layer was separated, washed with aqueous 1 m HCl (3 10 mL), driedover MgSO4 and concentrated under vacuum (40-methyl-2-biphenylcarboxaldehyde 2d was present in 70% estimated GC yield). Flashcolumn chromatography on silica gel (cyclohexane/ethyl acetate 9:1) afforded2d in 60% isolated yield
References:
Laval, Stéphane;Dayoub, Wissam;Pehlivan, Leyla;Métay, Estelle;Delbrayelle, Dominique;Mignani, Gérard;Lemaire, Marc [Tetrahedron Letters,2014,vol. 55,# 1,p. 23 - 26]
1940-19-8
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76293-17-9
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1713-63-9
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