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Synthesis method of massoia lactone

A technique of massoia lactone and a synthetic method, applied in the direction of organic chemistry and the like, can solve the problems of no commercial value, high cost of raw materials, cumbersome steps and the like

Active Publication Date: 2012-09-05
SHANGHAI AIPU VEGETABLE TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Most of the synthetic routes reported so far have cumbersome steps or high cost of raw materials and have no commercial value, so the spice has not yet been able to achieve large-scale industrial production

Method used

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  • Synthesis method of massoia lactone
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  • Synthesis method of massoia lactone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Step 1: Preparation of Ethyl Hexanoacetate

[0030] In a 5000ml three-neck flask equipped with mechanical stirring, a thermometer and a reflux tube, add 300g of ethyl acetoacetate, 3L of toluene, and 360g of magnesium ethoxide in sequence, react at room temperature for 1 hour, heat to reflux, and slowly add 350g of hexanoyl chloride dropwise for about 2 hours After dripping, add 200ml of 5% HCl after cooling, wash with 50ml of saturated sodium chloride, add 800ml of 25% ammonia water, react at room temperature for 2 hours, separate liquids, wash with dilute hydrochloric acid for 1 hour, wash with saturated sodium chloride, and water. Recover toluene, distill under reduced pressure, collect the components at 87-92 degrees / 1mmHg to obtain ethyl hexanoyl acetate with a yield of 82%.

[0031] Step 2: Preparation of 3-hexanoyl-6-pentyl-2H-pyran-2,4(3H)dione

[0032] Into a 2000mL three-necked flask, add 1000g of ethyl hexanoacetate obtained in step (1), 0.1g of sodium bicar...

Embodiment 2

[0043] Step 1: Preparation of Ethyl Hexanoacetate

[0044]In a 5000ml three-necked flask equipped with mechanical stirring, a thermometer and a reflux tube, add 300g of ethyl acetoacetate, 3L of tetrahydrofuran, and 380g of magnesium ethoxide in sequence, react at room temperature for 1 hour, heat to reflux, and slowly add 350g of hexanoyl chloride dropwise for about 2 hours After dripping, add 200ml of 5% HCl after cooling, wash with 50ml of saturated sodium chloride, then add 1000ml of 25% ammonia water, react at room temperature for 2 hours, separate liquids, wash with dilute hydrochloric acid for 1 hour, wash with saturated sodium chloride, and water. Recover toluene, distill under reduced pressure, collect 87-92 degree / 1mmHg component, yield 80%.

[0045] Step 2: Preparation of 3-hexanoyl-6-pentyl-2H-pyran-2,4(3H)dione

[0046] Add 1000g of ethyl hexanoacetate and 0.05g of sodium bicarbonate to a 2000mL three-necked flask, replace with nitrogen, react in a nitrogen strea...

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Abstract

The invention provides a synthesis method of massoia lactone. The massoia lactone is a rare spice which has cream fragrance, coconut fragrance, pungent fragrance and celery fragrance. The massoia lactone is prepared from hexanoic acid and acetoacetic ester as raw materials through five steps. All reactions involved in the process steps are classical fine chemical engineering unit reactions, the costs of raw materials and reagents are low, conditions are mild, and the yield of each step is higher. The process route provided by the invention has lower cost and is suitable for industrialized production.

Description

technical field [0001] The invention relates to a new process for synthesizing natural equivalent spices, in particular to a method for synthesizing massoia lactone. Background technique [0002] Massoia lactone is a precious spice with creamy, coconut, spicy, and celery aromas. It can be used in butter, cream, vanilla, peach, almond, fruit, nut, and tobacco flavor formulations. It exists in horse Soya osmanthus oil, white wine, osmanthus and cane molasses. There is no mature industrialization route for massoia lactone at present, the production scale is small, and the price is expensive. There is currently no domestic manufacturer producing it, and it mainly relies on imports. And massoia lactone is due to the rare content in nature, and the annual output is limited, which cannot satisfy people's pursuit of natural spices. Therefore, the development of massoia lactones synthesized from natural raw materials has become an urgent need. [0003] Massoia lactone was first is...

Claims

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Application Information

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IPC IPC(8): C07D309/32
Inventor 孟宪乐
Owner SHANGHAI AIPU VEGETABLE TECH
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