Monosaccharide geraniol carbonate diester compound, preparation method and use thereof
A technology of carbonic diester and geraniol, which is applied in the field of monosaccharide ester cigarette moisturizing agent, new cigarette moisturizing agent, and monosaccharide geraniol carbonic diester compound, can solve the problem of uneven fragrance release, low molecular weight, Loss of aroma and other problems, to achieve the effect of comfortable and harmonious aroma, high safety, and slowing down changes
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Embodiment 1
[0035] Embodiment 1: the synthesis of geraniyl chloroformate
[0036] Add 2000ml CH to the reaction flask 2 Cl 2 and bis(trichloromethyl)carbonate 129g (0.44mol), stirred at room temperature until the solid was completely dissolved, put the reaction bottle in an ice-salt bath, cooled to -10°C, added 1.28mol of geraniol, and dissolved completely , add 200ml of pyridine dropwise, control the rate of addition, and keep the temperature of the reaction solution at 0-5°C. After the dropwise completion, the reaction solution is naturally warmed to room temperature, stirred and reacted overnight, and the dichloromethane solution of geraniyl chloroformate is obtained. It can be used in the next reaction without purification, and the yield is quantitative.
Embodiment 2
[0037] Embodiment 2: the synthesis of geraniyl chloroformate
[0038] The operation process is the same as in Example 1, except that bis(trichloromethyl) carbonate is replaced with trichloromethyl chloroformate, pyridine is replaced with sodium bicarbonate, CH 2 Cl 2 Substitute toluene to obtain a toluene solution of geraniyl chloroformate, which can be used in the next reaction without purification, and the yield is quantitative.
Embodiment 3
[0039] Example 3: Preparation of 3,6-two-O-geraniol carbonyl-D-glucopyranose carbonate (compound I)
[0040]
[0041] Get 0.15 mol of the geraniyl chloroformate dichloromethane solution prepared in Example 1, add dropwise 9.7 g (0.05 mol) of D-glucosylmethyl glycoside and 20.2 g of triethylamine ( 0.20mol) and dichloromethane 100ml mixed solution, stirred at room temperature for 12h, after the reaction was completed, the solid was filtered out, the filtrate was evaporated to remove the solvent under reduced pressure, the residue was dissolved in 200ml of dichloromethane, 40ml of 20% hydrochloric acid aqueous solution was added, and the After stirring for 2h, the organic layer was washed successively with 50ml of saturated aqueous sodium carbonate solution and 50ml of saturated brine, and the obtained dichloromethane solution was washed with anhydrous Na 2 SO 4 Dry, filter, evaporate dichloromethane under reduced pressure, and purify the residue by silica gel column chromatog...
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