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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  • Abstract
  • Description
  • Claims
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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

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

Experimental program
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Example

[0017] example 1

[0018] Mix 1.76 millimoles (508 mg) of tetraethyl methylene diphosphate and 5 milliliters of a mixed solvent of tetrahydrofuran and toluene with a volume ratio of 1:3 and add 0.01 g of 2-hydroxy-4- Methoxy benzophenone, adjust the temperature to 10°C, then add 1.76 mmol of sodium methoxide, react for 20 minutes and add 1.01 mmol (208 mg) C dropwise 14 Aldehyde, continue the reaction for 10 minutes, add water equivalent to 20ml times the volume of the organic solvent, wash, dry, and distill under reduced pressure to obtain the final product 320mg, 3-methyl-5-(2,6,6-trimethyl-1-cyclo Hexen-1-yl)-2,4-pentadienyl diethyl succinate, with a yield of 93%, detected by gas chromatography,

[0019] The final product is tested 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 is greater than 99.999%

[0022] Column temperature 60℃→10℃ / Min→250℃(5Min)

[0023] Vaporizat...

Example

[0027] Example 2

[0028] Mix 1.76 millimoles (605 mg) of tetraisopropyl methylene diphosphate and 7 milliliters of a mixed solvent of tetrahydrofuran and toluene with a volume ratio of 1:4 and add to the reactor, add 0.01 g of 2-hydroxy-4- Octyloxybenzophenone, adjust the temperature to 10°C, then add 1.76 mmol sodium ethoxide, and after reacting for 20 minutes, add 1.41 mmol (290 mg) C dropwise 14 The aldehyde, continue to react for 15 minutes, add water equivalent to 25ml times the volume of the organic solvent, wash, dry, and distill under reduced pressure to obtain the final product 440mg, with a yield of 89%. , 6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienyl diisopropyl ester accounted for 85.8%. 3-Methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3-pentadienyl diisopropyl ester accounts for only 3.2%.

Example

[0029] Example 3

[0030] Mix 1.76 millimoles (605 mg) of tetraisopropyl methylene diphosphate and 7 milliliters of a mixed solvent of tetrahydrofuran and toluene with a volume ratio of 1:4 and add 0.01 g of 2-hydroxy-4- Octyloxybenzophenone, adjust the temperature to 20°C, then add 1.76 mmol sodium ethoxide, and after reacting for 20 minutes, add 1.41 mmol (290 mg) C dropwise 14 The aldehyde, continue to react for 15 minutes, add water equivalent to 25ml times the volume of the organic solvent, wash, dry, and distill under reduced pressure to obtain 430mg of the final product with a yield of 86.9%. The gas chromatography detects that 3-methyl-5-(2 , 6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienyl diisopropyl succinate accounted for 83.4%, 3-methyl-5-(2,6, 6-trimethyl-1-cyclohexen-1-yl)-1,3-pentadienyl diisopropyl ester accounts 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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