ChemicalBook CAS DataBase List 8,10-DODECADIEN-1-OL

8,10-DODECADIEN-1-OL synthesis

8synthesis methods

Product Name:8,10-DODECADIEN-1-OL
CAS Number:33956-49-9
Molecular formula:C12H22O
Molecular Weight:182.3

To a mixed so lution of Methyl5-oxo-(E,E)-8,10-dodecadienoate (15.7g, 0.07 mol) and p-toluene sulfonylhydrazine (16.3g, 0.0875 mol) in DMF - sulfolane (350ml, 1 : 1) was added p-toluenesulfonic acid (1.75g) and sodium cyanoborohydride (17.6g, 0.28mol) at room temperature, and the solution was heated at 100 ℃ for 4 hr. After cooling to room temperature, the reaction mixture was diluted with water (1000ml) and extracted with cyclohexane. The cyclohexane solution was washed with water, dried over Na2SO4 and concentrated in vacuo. Column chromatography of the oily residue over silica gel (Merck Kieselgel 60) with petroleum ether-ether (10:1) gave 4 (5.6g, 38%) as a pale yellow liquid.A solution of Methyl (E,E)-8,10-dodecadienoate (4.2g, 0.02mol) in absolute ether (40ml) was added dropwise to a slurry of lithium aluminum hydride (0.38g, 0.01mol) in absolute ether (60 ml) with stirring at room temperature. Stirring was continued for 1 hr at room temperature. After the mixture was refluxed for I hr, the reaction was quen ched with 2NH2SO4 (30ml) and the mixture was worked up by the usual procedure to give the alcohol 5, with a nearly quantitative yield, which solidified during storage in a refrigerator, (recrystallized from pe troleum ether). The purity was 97% on GLC analysis.

57006-69-6 Synthesis

Acetic acid (2E,4E)-2,4-hexadienyl ester

57006-69-6
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34714-00-6 Synthesis

34714-00-6
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33956-49-9
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Yield:33956-49-9 77.47%

Reaction Conditions:

Stage #1: (E,E)-sorbyl acetate;trimethylsilyl 6-chloro-1-hexyl etherwith sodium in toluene at 0 - 80; for 12 h;Inert atmosphere;Green chemistry;
Stage #2: with sulfuric acid in water;toluene at 0 - 20; for 1 h;Green chemistry;Temperature;

Steps:

1.C; 2.C Target product synthesis Example 1: E8, E10-dodecadien-1-ol

In a 1500L dry clean enamel reactor, enter 400kg of metered toluene, replace with nitrogen, put 46kg of chopped clean metal sodium, heat up to 80 ° C, cool under stirring, cool with ice water, cool to 10 ° C, drop by A mixture of intermediate B137 kg and intermediate C208.5 kg.Control 0-10 ° C drop, add dropwise, warm to 60 ° C, heat preservation reaction for 12 hours,Cool to 0 ° C, add 300 kg of water, 98 kg of sulfuric acid, control hydrolysis temperature 20 ° C, hydrolysis and stirring for 1 hour, check the water layer pH 3-4, layering, 200 kg of organic layer washed once, separate the water layer, organic layer negative pressure Concentrated to the solvent without, the remaining liquid enters the rectification column rectification, collecting 10mmHg, 118-120 ° C fraction, as shown in Figure 1,Detecting the E, E-isomer content of 99.5%,The quantity is: 141kg. The yield was 77.47%.The total yield was: 68%.

References:

CN110078593,2019,A Location in patent:Paragraph 0030; 0037; 0038; 0039; 0046; 0047