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Synthetic method for epoxy sclareol

A synthesis method and technology of sclareol, applied in the direction of organic chemistry and the like, can solve the problems of high cost, poor safety, explosion and the like, and achieve the effect of low product cost

Inactive Publication Date: 2007-12-26
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the obvious disadvantages of peracid as oxidizing agent are high cost, low atomic utilization rate, and relatively long reaction time.
In addition, many peroxyacids have poor stability, are easy to decompose during transportation, storage and use, and sometimes explode, and their safety is poor

Method used

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  • Synthetic method for epoxy sclareol
  • Synthetic method for epoxy sclareol
  • Synthetic method for epoxy sclareol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] 30.8g of sclareol was dissolved in 90mL of 1,2-dichloroethane, and 1.5g of 12-phosphotungstic acid, 0.72g of cetylpyridine chloride and 35mL of 30% aqueous hydrogen peroxide were added to adjust pH≈2.0 , the reaction was vigorously stirred at 70 °C for 12 hours. The obtained reaction mixture was separated and purified by conventional methods to obtain 30.4 g of epoxysclareol as a white solid with a yield of 93.8%. Melting point 131 ~ 132 ℃.

Embodiment 2

[0028] 30.8g of sclareol was dissolved in 60mL of chloroform, and 0.41g of sodium tungstate dihydrate, 0.72g of sodium dihydrogen phosphate, 0.36g of cetylpyridinium chloride and 90mL of 10% hydrogen peroxide solution were added to adjust pH≈1.5 , the reaction was vigorously stirred at 70 °C for 24 hours. The obtained reaction mixture was separated and purified by conventional methods to obtain 28.4 g of epoxysclareol as a white solid with a yield of 87.8%. Melting point 130 ~ 132 ℃.

Embodiment 3

[0030] 30.8 g of sclareol was dissolved in 60 mL of ethyl acetate, 2.0 g of hexadecylphosphotungstic acid pyridinium salt and 21 mL of 50% aqueous hydrogen peroxide solution were added, and the reaction was vigorously stirred at 70° C. for 8 hours. The obtained reaction mixture was separated and purified by conventional methods to obtain 30.2 g of epoxysclareol as a white solid with a yield of 93.2%. Melting point 130 ~ 132 ℃.

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Abstract

The epoxy sclareol is synthesized with sclareol as main material, hydrogen peroxide solution as oxidant, and water and / or organic solution of transition elements, especially VB or VIB transition elements as the catalyst for activating hydrogen peroxide. Inside the homogeneous or two-phase water-organic solvent system, there is also of kind of phase transfer catalyst, so as to epoxidize sclareol into epoxy sclareol and to obtain epoxy sclareol through conventional separation and purification. Compared with available technology, the present invention uses cheap and clean hydrogen peroxide aqua as oxidant and has the advantages of simplicity, cleanness, high efficiency, high safety and low cost.

Description

technical field [0001] The invention relates to a method for synthesizing epoxy compounds, in particular to a method for synthesizing epoxysclareol. Background technique [0002] Epoxy sclareol is a synthetic fragrance ambroxan [chemical name 1, 2, 3a] synthesized from sclareol [chemical name 8α, 13-dihydroxy-15, 16-didehydrolabydan] , 4,5,5a,6,7,8,9,9a,9b-decahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan, trade name Ambrox, Ambroxan, Amberoxide, etc.] and sclareolide [chemical name is 1,2,3a,4,5,5a,6,7,8,9,9a,9b-dodecahydro-3a,6,6,9a-tetramethyl An important intermediate for naphtho[2,1-b]furan-2(1H)-one]. Epoxy sclareol is also an important raw material for the preparation of sclareol [chemical name is 8α, 13, 14, 15-tetrahydroxy-reiberdan]. [0003] In previously reported methods, epoxysclareol was synthesized by epoxidizing sclareol using organic peroxyacids as oxidants. The synthesis method disclosed in the German patent (DE4 124 726) is the epoxidation of sclareol...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D303/14
Inventor 魏俊发吴亚石先莹张勇民
Owner SHAANXI NORMAL UNIV
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