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Method for preparing 3-methyl-5-(2,6,6-trimethyl-1-cyclohexene-1-base)-2, 4-pentadiene-dialkyl phosphoric ester

A technology of dialkyl pentadienyl phosphonate and tetraalkyl methylene diphosphate, which is applied in the field of 3-methyl-5--2, can solve the problem that the conversion rate is only 76%, and the yield of the target product is reduced. The efficiency and difficulty of separating the target product increase, and achieve the effect of benefiting industrial production, reducing energy consumption and difficulty of production operation

Inactive Publication Date: 2008-12-10
GUANGZHOU WISDOM BIO TECH
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Problems solved by technology

[0005] The preparation method of this compound is described in U.S. Patent Phosphonate Reagent Compositions (US4916250), and this method uses carbon tetradecaldehyde and methylene diphosphate tetraethyl ester to react under the effect of organic solvent and alkali metal salt to generate 3-methyl-5 -(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2,4-pentadienyl phosphonic acid dialkyl ester, as shown in Formula 2, but the final product of this method In addition to the target product, it also contains a large amount of 3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3-pentadienylphosphonic acid di Alkyl esters account for almost half of the final product, which greatly reduces the yield of the target product and increases the difficulty of separating the target product; although this method also provides 3-methyl-5-(2,6,6 -Trimethyl-1-cyclohexen-1-yl)-1,3-pentadienyl dialkyl ester is converted into 3-methyl-5-(2,6,6-trimethyl- 1-cyclohexen-1-yl)-2,4-pentadienyl dialkyl dialkyl ester, but the conversion rate is only 76%

Method used

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  • Method for preparing 3-methyl-5-(2,6,6-trimethyl-1-cyclohexene-1-base)-2, 4-pentadiene-dialkyl phosphoric ester
  • Method for preparing 3-methyl-5-(2,6,6-trimethyl-1-cyclohexene-1-base)-2, 4-pentadiene-dialkyl phosphoric ester
  • Method for preparing 3-methyl-5-(2,6,6-trimethyl-1-cyclohexene-1-base)-2, 4-pentadiene-dialkyl phosphoric ester

Examples

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example 1

[0018] 1.76 millimoles (508 milligrams) of tetraethyl methylene diphosphate and 5 milliliters of a mixed solvent of tetrahydrofuran and toluene with a volume ratio of 1:3 were mixed and added to the reactor, and 0.01 g of 2-hydroxyl-4- Methoxybenzophenone, adjust the temperature to be 10°C, then add 1.76 mmoles of sodium methylate, and drop 1.01 mmoles (208 mg) of C after 20 minutes of reaction 14 Aldehydes, after continuing to react for 10 minutes, add water equivalent to 20ml times the volume of the organic solvent to wash, dry, and distill under reduced pressure to obtain 320mg of the final product, 3-methyl-5-(2,6,6-trimethyl-1-cyclo Hexen-1-yl)-2,4-pentadienyl diethyl diacetate, the yield was 93%, detected by gas chromatography,

[0019] The final product is detected by gas chromatography under the following chromatographic conditions:

[0020] Capillary column SE-54 (30m*0.25mm*0.25um)

[0021] Carrier gas is N 2 Purity greater than 99.999%

[0022] Column temperatur...

example 2

[0028] 1.76 millimoles (605 milligrams) of tetraisopropyl methylene diphosphate and 7 milliliters of a mixed solvent of tetrahydrofuran and toluene with a volume ratio of 1:4 were mixed and added to the reactor, and 0.01 grams of 2-hydroxyl-4- Octyloxybenzophenone, adjust the temperature to be 10°C, then add 1.76 mmoles of sodium ethylate, and drop 1.41 mmoles (290 mg) of C after 20 minutes of reaction 14 Aldehyde, after continuing to react for 15 minutes, add water equivalent to 25ml times the volume of the organic solvent to wash, dry, and distill under reduced pressure to obtain 440 mg of the final product, with a yield of 89%. Detected by gas chromatography, 3-methyl-5-(2 , 6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienyl diisopropyl phosphonate accounted for 85.8%. Diisopropyl 3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3-pentadienylphosphonate accounted for only 3.2%.

example 3

[0030] 1.76 millimoles (605 milligrams) of tetraisopropyl methylene diphosphate and 7 milliliters of a mixed solvent of tetrahydrofuran and toluene with a volume ratio of 1:4 were mixed and added to the reactor, and 0.01 grams of 2-hydroxyl-4- Octyloxybenzophenone, adjust the temperature to be 20°C, then add 1.76 mmoles of sodium ethylate, and drop 1.41 mmoles (290 mg) of C after 20 minutes of reaction 14 Aldehydes, after continuing to react for 15 minutes, add water equivalent to 25ml times the volume of the organic solvent to wash, dry, and distill under reduced pressure to obtain 430mg of the final product, with a yield of 86.9%. Detected by gas chromatography, 3-methyl-5-(2 , 6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienyl diisopropyl phosphonate accounted for 83.4%, 3-methyl-5-(2,6, Diisopropyl 6-trimethyl-1-cyclohexen-1-yl)-1,3-pentadienylphosphonate accounted for only 3.5%.

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Abstract

The invention provides a method for preparing 1, 3-methyl-5-(2, 6, 6-trimethyl-1- cyclohexene-1-yl)-2, 4-pentadiene methyl phosphonate. In the method, a benzophenone compound preventing transposition is added in the process of generating the 1, 3-methyl-5-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4-pentadiene methyl phosphonate by the reaction of methylene diphosphate four alkyl and C14 aldehyde in a mixed solvent of methylbenzene and tetrahydrofuran, thereby inhibiting the generation of a target product isomer in order that the content of the target product in a final product reaches up to 97 percent.

Description

technical field [0001] The present invention relates to the field of organic chemistry, in particular to 3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienyl dioxane Method for the preparation of base esters. Background technique [0002] 3-Methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienyl dialkyl ester is the preparation of vitamin A, vitamin A Derivatives and key intermediates of β-carotene, the chemical structure of which is shown in Formula 1: [0003] [0004] (Where R1, R2 are the same or different hydrocarbon groups with less than 5 carbon atoms) [0005] The preparation method of this compound is described in U.S. Patent Phosphonate Reagent Compositions (US4916250), and this method uses carbon tetradecaldehyde and methylene diphosphate tetraethyl ester to react under the effect of organic solvent and alkali metal salt to generate 3-methyl-5 -(2,6,6-Trimethyl-1-cyclohexen-1-yl)-2,4-pentadienyl phosphonic acid dialkyl ester, as shown in Formu...

Claims

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Application Information

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IPC IPC(8): C07F9/40
Inventor 吴世林邸维龙
Owner GUANGZHOU WISDOM BIO TECH
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