Damascenone CAS 23696-85-7

Liquify 10.0 g (52mmol) of α-ionone in 20mL of ethanol and include it to the flask. Include 3.8 g (60mmol) of hydroxylamine hydrochloride, 6.4 g (70mmol) of sodium acetate and 15mL of deionized water to the flask in sequence. After the enhancement is ended up, the system temperature level is elevated to 55 ° C, and the response time is controlled for 3 hours. After the reaction, 60 mL of deionized water was included in the system, extracted 3 times with 60 mL of ethyl acetate, and the organic stages were incorporated. The all-natural stage was cleaned with 60 mL of saturated salt bisulfite aqueous option, dried out over anhydrous MgSO4, and the solvent was vaporized to acquire an orange liquid, which was placed in a fridge to end up being a solid, which is α-ionone oxime compound 2, with a return of 99.6%. The molecular weight of substance 2 was developed to be 207 by gas chromatography mass spectrometry, which followed the calculated molecular weight of α-ionone oxime. The hydrogen nuclear magnetic spectrum discloses that there are 22 hydrogens, including 4 methyl groups. The chemical changes δH are 2.00, 1.55, 0.89, and 0.81 particularly. The chemical shifts δH of the three alkene hydrogens are 6.12, 5.86, and 5.42 specifically. The NMR carbon variety reveals that it has 13 carbons, including 1 oxime group, the chemical change δC is 155.7, and the chemical adjustments δC of the 4 alkene carbons are 136.5, 132.8, 127.9, and 120.9 respectively. The product was identified to be α-ionone oxime by combining gas chromatography mass spectrometry and nuclear magnetic assessment.

Consist of 5.1 g (24mmol) α-ionone oxime 2 to 70mL of deionized water, include it to the feedback container, and preserve the system temperature level at 0 ° C. While blending, gradually include 3.7 mL LCTAOH (10wt%), and the system modifies from anemic and clear to milky white liquid. Then gradually include a mixture of 35mL hydrogen peroxide (30%) and 5mL lithium hydroxide (6mol/L). After the addition is finished, the system The temperature rose to 25 ° C and the reaction time was 15h. After the response is finished, add 150 mL of deionized water, remove 3 times with 100 mL of methylene chloride, integrate the natural phases, completely dry with anhydrous MgSO4, and vaporize the solvent to obtain α-ionone epoxy oxime substance 3, with a return of 98.8 %.

Include 4.0 g (19mmol) α-ionone isoxazole got 4, 70mL cyclohexane and 2.0 g (86mmol) Na into the three-necked flask. Protect the system temperature at 40 ° C and consist of 8mL outright ethanol up till there is no steel left. After the salt continues to be, the response time is 8 hours; after the response is ended up, include 6g ammonium chloride and 30mL of deionized water, and the remedy is extracted three times with 50mL of methylene chloride, integrate the natural phases, and afterwards wash with 50mL of saturated sodium bicarbonate liquid choice. Dry with water and MgSO4; the fluid after evaporating the solvent is after that distilled under reduced stress and anxiety to obtain α-damascenone with a return of 90.8%.