ChemicalBook CAS DataBase List 1-Nonanal

1-Nonanal synthesis

12synthesis methods

Product Name:1-Nonanal
CAS Number:124-19-6
Molecular formula:C9H18O
Molecular Weight:142.24

By catalytic oxidation of the corresponding alcohol (n-nonanol) or reduction of the corresponding acid

112-62-9 Synthesis

112-62-9
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124-19-6
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1931-63-1
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Yield:1931-63-1 100% ，124-19-6 100%

Reaction Conditions:

Stage #1: (Z)-9-octadecenoic acid methyl esterwith ozone in dichloromethane at -78;
Stage #2: with triphenylphosphine in dichloromethane at -78 - 23; for 18 h;

Steps:

4

A solution of methyl oleate ( 10.0 g, 33.7 mmol) in anhydrous CH₂Cl₂ ( 100 mL) was cooled to -78 °C and a stream of O₃ was bubbled through the reaction mixture until the solution became lightly blue ( 10 min). Argon was bubbled through the mixture and a solution of PPh₃ (19.7 g, 75.1 mmol) in CH₂Cl₂ (100 mL) was added slowly. The reaction mixture was warmed to 23 ⁰C and stirred for 18 hours. The solvent was evaporated to dryness and the solid was triturated with cold hexane (80 mL). The EPO filtrated was evaporated to give a yellow oil. The oil was purified by chromatography on silica gel (CH₂Cl₂:Hex, 1 : 1 and then CH2Cl2:Et2θ, 1 : 1) to provide the two expected aldehydes, nonanal (4.80 g, 100%) and methyl 8-formyloctanoate 12 (6.28 g, 100%), both as colourless oils. ¹H NMR (300 MHz, CDCl₃) δ 9.76 (s, IH), 3.66 (s, 3H), 2.41 (t, J= 7.3 Hz, 2H), 2.30 (t, J= 7.3 Hz, 2H), 1.61 (m, 4H), 1.31 (m, 6H). ¹³C NMR (75 MHz, CDCl₃) δ 202.4, 173.8, 51.1 , 43.5, 33.7, 28.7, 28.6, 28.5, 24.5, 21.7. MS (APCI): 187 (M+ l)⁺. Rf= 0.2 (CH₂Cl₂).