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Synthesis method of (+/-)-lavandulol

A synthetic method, the technology of lavandulol, which is applied in the field of organic synthesis, can solve the problems of incapability of large-scale industrial production, limitation of application of lavandulol, cumbersome synthesis steps, etc., and achieve the effects of convenient industrial production, low production cost and high reaction yield

Pending Publication Date: 2022-04-22
CHINA TOBACCO ANHUI IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, there are few methods for synthesizing (±)-lavandulol, mainly through Claisen rearrangement reaction (Matsui, M.; Stalla-Bourdillon, B. Agric. Biol. Chem. 1968, 32, 1246-1249) and Prins reaction (Cookson , R.C.; Mirza, N.S.Synth.Commun.1981,11,299-301.) synthesis, but because of its cumbersome synthesis steps and harsh conditions, it cannot be industrialized in large quantities, which greatly limits the application of lavandulol

Method used

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  • Synthesis method of (+/-)-lavandulol
  • Synthesis method of (+/-)-lavandulol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1: Synthesis of ethyl 2-acetyl-5-methylhex-4-enoate

[0022] Add ethyl acetoacetate (50mmol), 1-bromo-3-methyl-2-butene (60mmol), potassium carbonate (75mmol) and potassium iodide (40mmol) into a 250mL reaction flask in sequence, add N,N-dimethyl Dimethyl formamide (100 mL) and started stirring to make it evenly stirred. The reaction was stirred at room temperature for 24 hours. After the raw materials disappeared completely, the stirring was stopped. The reaction mixture was washed successively with water (100 mL×3) and saturated brine (100 mL), and the organic phases were combined and dried over anhydrous magnesium sulfate (5 g). The insoluble matter was removed by filtration, and the excess organic solvent was removed by concentration under reduced pressure to obtain ethyl 2-acetyl-5-methylhex-4-enoate, which was directly used in the next reaction without purification.

Embodiment 2

[0023] Embodiment 2: the synthesis of ethyl lavender

[0024] In a 250 mL round bottom flask, add 2-acetyl-5-methylhex-4-enoic acid ethyl ester 3 and methyl Wittig reagent (50 mmol) successively, and add toluene (100 mL) to dissolve, and the reaction is stirred at room temperature for 72 hours . After the reaction was completed, diethyl ether (100 mL) was added, insoluble impurities were removed by filtration, excess organic solvent was removed by concentration under reduced pressure, and the crude product was purified by column chromatography (the eluent volume ratio was petroleum ether:ethyl acetate=50:1), Ethyl lavender (6.08 g, yield 62%) was obtained.

Embodiment 3

[0025] Embodiment 3: the synthesis of lavandulol

[0026] In a 250mL round-bottomed flask, add ethyl lavender (31mmol) obtained in the previous step, add ether (100mL) to dissolve, cool the reaction mixture to 0°C, and add lithium aluminum hydride (93mmol) batch by batch to the reaction. The reaction was slowly warmed to room temperature and stirred at room temperature for 6 hours. After the reaction is completed, add sodium sulfate decahydrate (NaSO 4 10H 2 (2, 300mmol) quenched the reaction, filtered to remove insoluble impurities, and the filter cake was washed with ether (100mL), the organic phases were combined and dried with anhydrous magnesium sulfate (10g), concentrated under reduced pressure to remove excess organic solvent, and the crude product was purified by column chromatography (The volume ratio of the eluent is petroleum ether:ethyl acetate=3:1) to obtain lavandulol (4.39 g, yield 92%).

[0027] 1 H NMR (600MHz, CDCl 3 )δ5.03(tt, J=7.9, 1.3Hz, 1H), 4.91-4....

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Abstract

The invention discloses a synthesis method of (+ / -)-lavandulol. The synthesis method comprises the following steps: (1) carrying out substitution reaction on ethyl acetoacetate and 1-bromo-3-methyl-2-butene under an alkaline condition to prepare 2-acetyl-5-methylhex-4-olefine acid ethyl ester; (2) carrying out a Wittig reaction on the ethyl 2-acetyl-5-methylhexyl-4-olefine acid ester and a methyl Wittig reagent in an organic solvent, so as to prepare ethyl lavandulamate; and (3) reducing the ester group of the ethyl lavandulate into alcohol under the action of lithium aluminum hydride to prepare the final product (+ / -)-lavandulol. The method has the advantages of low raw material price, short process route, few post-treatment steps and high reaction yield, and is a production process with a relatively good production prospect.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a method for synthesizing (±)-lavandulol. Background technique [0002] (±)-Lavenderol, also known as Lavanditol, is an important terpene-like natural fragrance raw material, widely present in lavender oil, miscellaneous lavender oil, spike lavender oil and some natural essential oils, and is one of the evaluation methods for lavender oil. An important indicator component. Lavender alcohol has a lavender-like floral aroma with a green spicy smell, and can be used in the field of daily chemical essence. Because of its low content in general lavender oil, the extraction rate of (±)-lavandulol from natural essential oils is not high and the price is high, which is not economically realistic, so it is generally synthesized by chemical synthesis (±) - Lavandol. [0003] At present, there are few methods for synthesizing (±)-lavandulol, mainly through Claisen rearrangement...

Claims

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Application Information

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IPC IPC(8): C07C29/147C07C33/02
CPCC07C29/147C07C67/30C07C67/343C07C33/02C07C69/587C07C69/738
Inventor 王文斌王海洋贺增洋邹鹏王薛邵宁刁洪林
Owner CHINA TOBACCO ANHUI IND CO LTD
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