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Method for producing farnesal using vanadium complex

A manufacturing method and technology of farnesal, which is applied in the field of new vanadium complexes and its manufacture, can solve the problems of farnesal being expensive, poor in efficiency, impossible to implement, etc.

Active Publication Date: 2014-09-03
SAGAMI CHEM RES CENT +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] The existing (2E, 6E)-farnesal manufacturing method that uses (E)-nerolidol has the following disadvantages: it cannot be implemented industrially, or the efficiency is poor, and the resulting (2E, 6E)-farnesal expensive

Method used

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  • Method for producing farnesal using vanadium complex
  • Method for producing farnesal using vanadium complex
  • Method for producing farnesal using vanadium complex

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0111] Examples are given below to clarify the embodiment of the present invention, but the present invention is not limited to the examples shown here.

[0112] The reaction solution obtained in the examples was analyzed by gas chromatography, and the purity of (2E, 6E)-farnesal and (2Z, 6E)-farnesal was calculated by area percentage. Measurement conditions are as follows.

[0113]Device: GC-14A (Shimadzu Corporation)

[0114] Column: HP-ULTRA1 (Agilent Technologies)

[0115] 25m×I.D.0.32mm, 0.52μmdf

[0116] Column temperature: 100°C→[10°C / min]→250°C

[0117] Injection temperature: 250°C

[0118] Carrier Gas: Helium

[0119] Detector: Hydrogen Flame Ionization Detector (FID)

[0120] In addition, the measurement conditions of the NMR spectra of the compounds isolated in Reference Examples and Examples are as follows.

[0121] Preparation of mixtures with compound and deuterated CDCl 3 (manufactured by Cambrige Isotope Laboratories, Inc., containing 0.05% TMS), using ...

reference example 1

[0123]

[0124] Bis(acetylacetonate)vanadium(IV) oxide (3.64 g, 20.6 mmol) was suspended in 2-propanol (100 mL), and 8-hydroxyquinoline (5.97 g, 41.1 mmol) was added. After stirring this at room temperature for 7 hours, the precipitated crystals were filtered and washed with 2-propanol (20 mL). The obtained wet crystals were dried under reduced pressure at 40° C. for 17 hours to obtain the vanadium complex (hereinafter referred to as “i-Pr complex”) represented by the above formula (2-1) (6.42 g, product rate of 75.2%).

[0125] 1 H-NMR (400MHz, CDCl 3 )δ8.60(s, 1H), 8.46(s, 1H), 8.09(d, 1H, J=8.0Hz), 8.02(d, 1H, J=8.4Hz), 7.51-7.56(m, 2H), 7.15-7.22(m, 6H), 6.26-6.32(m, 1H), 1.53(d, 3H, J=11.6Hz), 1.49(d, 3H, J=6.4Hz)

manufacture Embodiment 1

[0127]

[0128] Synthesis of the vanadium complex shown in

[0129] Bis(acetylacetonate)vanadium(IV) oxide (182 mg, 0.69 mmol) was suspended in acetonitrile (5 mL), and 8-hydroxyquinoline (199 mg, 1.37 mmol) and phenol (5 mL) were added thereto. This was stirred at room temperature for 6 hours, and the solvent was distilled off under reduced pressure. After adding diisopropyl ether (10 mL) to the residue, the precipitated crystals were filtered and washed with diisopropyl ether (5 mL). The obtained wet crystals were dried under reduced pressure at 40° C. for 7 hours to obtain the vanadium complex represented by the above formula (2a-1) (264 mg, yield 85.7%).

[0130] 1 H-NMR (400MHz, CDCl 3 )δ8.64(d, 1H, J=4.4Hz), 8.49(d, 1H, J=3.2Hz), 8.15(d, 1H, J=7.2Hz), 8.04(d, 1H, J=7.2Hz) , 7.54-7.60(m, 2H), 7.27-7.31(m, 6H), 7.17-7.23(m, 4H), 6.95-6.99(m, 1H)

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Abstract

Provided is a method for producing farnesal that is useful as an intermediate for the production of a medicinal agent, an agrichemical and a flavoring agent. Specifically provided is a method for producing farnesal (3), characterized by reacting (E)-nerolidol (1) with an oxidizing agent in the presence of a vanadium complex represented by general formula (2) (wherein R1 to R7 are as defined in the description and claims).

Description

technical field [0001] The present invention relates to a method for producing farnesal from (E)-nerolidol using a vanadium complex. In addition, the present invention relates to a novel vanadium complex and a method for producing the same. Background technique [0002] Farnesal (3,7,11-trimethyl-2,6,10-dodecatrienal) is known to be an important compound used as an intermediate in the production of pharmaceuticals, agricultural chemicals, fragrances, and the like. In particular, (2E,6E)-farnesal can be used as an intermediate for the production of polyisoprene derivatives useful as anticancer agents and the like (see, for example, Patent Document 1). There are four isomers of (2E,6E)-body, (2Z,6E)-body, (2E,6Z)-body and (2Z,6Z)-body in farnesal, so for the selective production of ( 2E,6E)-farnesal methods have been studied in various ways. [0003] For example, the following method is disclosed: using (2E,6E)-farnesol ((2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-ol) as ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/34C07C47/21B01J31/22C07B61/00
CPCC07B61/00C07C45/512C07C45/34B01J31/22C07C47/21C07F9/005B01J31/2243B01J2231/70B01J2531/56B01J31/2273B01J2540/40C07C45/29C07C45/37
Inventor 井上宗宣荒木宏史田中豪
Owner SAGAMI CHEM RES CENT
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