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Synthetic method of menthofuran

A synthesis method, the technology of mentha furan, which is applied in the field of synthesis of mentha furan, achieves the effects of improving the three wastes and operating conditions, mild reaction conditions, and simple post-treatment and purification processes

Inactive Publication Date: 2012-05-16
SHANGHAI WANXIANG FLAVORS & FRAGRANCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The technical problem to be solved by the present invention is to provide a synthetic method of menthafuran with easy-to-obtain raw materials, simple operation and less pollution in view of the problems existing in the existing menthafuran synthesis method

Method used

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  • Synthetic method of menthofuran
  • Synthetic method of menthofuran

Examples

Experimental program
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Effect test

Embodiment 1

[0033] 1) Synthesis of isopulegol epoxide

[0034] Install an electric stirring device on a 2000ml four-necked bottle and place it in a water bath, and install a thermometer on a constant-pressure separating funnel and place it in an ice-water bath.

[0035] Add 900ml of acetone, 1g of manganese sulfate, 31g of acetonitrile, 185g of isopulegol, and 30g of anhydrous sodium carbonate into a 2000ml four-necked bottle under stirring; Add 516g of 30% hydrogen peroxide dropwise into a 2000ml four-neck bottle with a liquid funnel, keep the temperature below 35°C, and finish the dropwise addition in about 4 hours. Continue to stir for 1 hour. The reaction is complete by gas chromatography; the potassium iodide-starch test paper detects no discoloration. The solvent was evaporated under normal pressure, the lower water phase was let stand, the oil phase was washed with water, and the oil pump was distilled under reduced pressure to obtain 167.5 g of isopulegol epoxide (94-104° C. / 600 P...

Embodiment 2

[0041] 1) Synthesis of isopulegol epoxide

[0042] Install an electric stirring device on the 500ml four-necked bottle and place it in a water bath, and install a thermometer on a constant-pressure separating funnel and place it in an ice-water bath.

[0043]Add 200ml acetone, 15ml aqueous solution of 0.8g manganese sulfate, 10g acetonitrile, 55g isopulegol, and 8g sodium bicarbonate to a 500ml four-necked bottle with stirring; add 150g 28% hydrogen peroxide dropwise, and keep it below 38°C for about 3 hours After the dropwise addition, continue to stir for 1 hour; the potassium iodide-starch test paper detects no discoloration. The solvent was evaporated under normal pressure, the lower water phase was let stand, the oil phase was washed with water, and the oil pump decompressed distillation to obtain 49.2g of isopulegol epoxide (94-104°C / 600Pa); the yield was 81%.

[0044] 2) Synthesis of isopulegone epoxide

[0045] Install an electric stirring device on a 1000ml three-ne...

Embodiment 3

[0049] 1) Synthesis of isopulegol epoxide

[0050] Install an electric stirring device on the 500ml four-necked bottle and place it in a water bath, and install a thermometer on a constant-pressure separating funnel and place it in an ice-water bath.

[0051] Add 200ml of methanol, 0.6g of manganese sulfate, 9g of acetonitrile, 47g of isopulegol, and 8g of sodium bicarbonate into a 500ml four-necked bottle under stirring; Add 130g of 30% hydrogen peroxide dropwise into a 2000ml four-necked bottle with a liquid funnel, keep the temperature below 38°C, complete the dropwise addition in about 3 hours, and continue stirring for 1 hour; the potassium iodide-starch test paper did not change the color. The solvent was distilled off under normal pressure, the lower water phase was let stand to release, the oil phase was washed with water, and the oil pump decompressed distillation to obtain 41g of isopulegol epoxide (94-104°C / 600Pa); the yield was 79%.

[0052] 2) Synthesis of isopul...

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Abstract

The present invention relates to a synthetic method of menthofuran, which takes isopulegol as a raw material. The method comprises the following steps: A. epoxidation reaction: isopulegol is reacted with perhydrol under the effect of a catalyst to obtain an isopulegol epoxide; B. oxidation reaction: the isopulegol epoxide is oxidized by a chlorate oxidant under existence of an acid medium to obtain an isopulegone epoxide shown in the formula III; C. cyclization reaction: the isopulegone epoxide is dehydrated and cyclized under the existence of the acid medium to obtain the target product menthofuran shown in the formula IV. The synthetic method of the present invention has the advantages that the raw material is easy to acquire, the reaction conditions are mild, three-waste situation and operation conditions can be greatly improved and the comprehensive lost is low. The synthetic route is shown as follows.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for synthesizing menthol furan. technical background [0002] Mentha furan is a natural fused ring and oxygen-containing heterocyclic compound present in Mentha plants. As a minor but characteristic component of peppermint oil, its characteristic odor is difficult to be replaced by other compounds, so Menthofuran is very important in some essential oil formulations and supplement formulations. Its synthesis has long attracted people's attention, but at present menthofuran is still expensive and not easy to obtain. [0003] Reports such as S.C.Taneja (Indian J.chem.Vol.19B 714,1980) take isopulegone or pulegone as the starting material, after halogenation (NBS / CCl4 or iodine), in the methanol solution of sodium hydroxide Cyclization under action gives the product. Because isopulegone is expensive, plus the toxicity of using NBS, the use of carbon tetrachlor...

Claims

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Application Information

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IPC IPC(8): C07D307/79
Inventor 黄战鏖何佳侯峰张长征钱正刚
Owner SHANGHAI WANXIANG FLAVORS & FRAGRANCES
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