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ChemicalBook CAS DataBase List 1-Nonanal
124-19-6

1-Nonanal synthesis

12synthesis methods
By catalytic oxidation of the corresponding alcohol (n-nonanol) or reduction of the corresponding acid
-

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).

References:

WO2006/117197,2006,A1 Location in patent:Page/Page column 14; 20-21

1-Nonanal Related Search:

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