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Solanesyl bromine preparation process and its refining method

The technology of a preparation process and a purification method is applied to the preparation process of solanesyl bromide and the purification field thereof, and can solve the problems of reduced yield, easy decomposition, long column chromatography and the like, achieves large production capacity, and eliminates waste water discharge. Volume and easy operation

Inactive Publication Date: 2006-04-26
YUNNAN KEEN BIOENG
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Problems solved by technology

However, solanesyl bromide is an unstable compound, and it is easy to cause decomposition during the purification process of column chromatography, so it must be carried out in the shortest possible time with a shorter chromatographic column.
In mass production on an industrial scale, column chromatography takes a long time, and solanesyl bromide will be decomposed by being adsorbed by silica gel for a long time, resulting in a decrease in yield

Method used

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  • Solanesyl bromine preparation process and its refining method
  • Solanesyl bromine preparation process and its refining method

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Embodiment

[0017] Chemical reaction equation:

[0018]

[0019] figure 1 In, solanesol 74g (purity 85%), 260ml n-hexane, 2.2ml pyridine, stirring and dissolving, temperature-10~10 ℃ under stirring, the 40ml n-hexane solution of 4.4ml phosphorus tribromide is added dropwise in 30 minutes, then The stirring reaction was continued at the same temperature for 2 hours. 200 ml of acetonitrile was added for washing three times, and the solvent was evaporated under reduced pressure to obtain 71 g of solanesyl bromide with a yield of 98% (calculated as pure solanesol) and a purity of 97%.

[0020] NMR (CDCl 3 ): δ1.63(24H, s), 1.68(3H, s), 1.73(3H, J=1Hz s), 1.96~2.10(32H, m), 4.02(2H, d, J=8.3Hz), 5.10 ~5.13 (8H, m), 5.53 (1H, t, J=8.3Hz).

[0021] Stir and dissolve 53g solanesol in a mixed solvent of 50ml petroleum ether (b.p40~45℃) and 70ml anhydrous ether, then add 1.8ml pyridine, stir at 0~10℃ for 1 hour, add dropwise 3.5ml phosphorus tribromide 20ml of petroleum ether solution, then...

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Abstract

The present invention relates to the preparation process and refining method of solano bromide. Solano bromide is prepared with solanesol as initial material and the preparation process includes the main steps of bromination with phosphorus tribromide in non-polar solvent and subsequent direct washing with polar solvent to refine. The said refining method has no extraction, drying, chromatographic column refining and other steps and thus has no emulsification, decomposition, so that the present invention has high product yield and purity and lowered cost.

Description

technical field [0001] The invention relates to a novel preparation process and refining method of solanesyl bromide. Background technique [0002] solanes bromide Chemical name: 1-Bromo-3, 7, 11, 15, 19, 23, 27, 31, 35-nonamethyl-2, 6, 10, 14, 18, 22, 26, 30, 34-36 Alkane-nonacene] is a medicine such as antineoplastic drug, coenzyme Q n , Vitamin K n important synthetic intermediates. The most direct synthesis method of solanesyl bromide is the raw material solanesol extracted from tobacco Bromide is obtained. For example: the method using triphenylphosphine and carbon tetrabromide [Yōji Mimaki, Hiroyuki Yamazaki, Hiroyuki Ikemoto, JP Ping 8-109146]; the method using pyridine and phosphorus tribromide [R.Ruegg, U.Gloor, G Ryser, O. Isler, Helv. Chim. Acta, 42, 2616 (1959)]. This method is beneficial for keeping the all-trans configuration of the isoprene chain, but in the post-treatment process, water and ether extraction are added, and the impurity in solanesyl br...

Claims

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Application Information

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IPC IPC(8): C07C21/14C07C17/16
Inventor 张建臣
Owner YUNNAN KEEN BIOENG
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