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Synthetic method for 4-(1, 5-dimethyl-1-vinyl-4-hexenyl) phenol

A synthesis method and vinyl technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of complex reaction conditions, many synthesis steps, expensive reagents, etc., and achieve simple operation, cheap reagents, reaction The effect of fewer steps

Inactive Publication Date: 2005-10-19
GUANGZHOU INST OF GEOCHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
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  • Application Information

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Problems solved by technology

At present, the synthesis of this substance has been reported, and the literature (Enantiomer 1997, 2, 297; Tetrahedron: Asymmetry 1999, 10, 1153; J.Chem.Res. 2000, 530; TetrahedronLetters 2002, 43, 4641) on 4- The chemical synthesis of (1,5-dimethyl-1-vinyl-4-hexenyl)phenol has been reported in detail, but the synthetic methods provided in these documents have many synthetic steps, mostly within 5 to 15 Between steps, the reaction conditions are complicated, the reagents used are expensive, and the yield is also low

Method used

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Embodiment Construction

[0013] 1, Preparation of 3-vinyl citronellal

[0014] Put 15.4g (0.1mol) of geraniol and 9.5g (0.03mol) of mercuric acetate in a 250ml round bottom flask, then add 72g (1mol) of newly distilled vinyl ether, blow nitrogen, then cool to 0°C and react for 24 hours . followed by 10% Na 2 CO 3 After the aqueous solution was reacted for 0.5 hours, the organic phase was extracted with ether, dried over anhydrous sodium sulfate, and the solvent was evaporated. The residue was heated to 180°C in an oil bath and kept for 0.5 hours. The product was chromatographed on a silica gel column (petroleum ether / chloroform=1 / 2) to obtain 9.38 g of aldehyde (2), with a yield of 52.1%.

[0015] IR (film): 1722, 1452, 1378, 1004, 917cm -1 ; 1 H NMR (CDCl 3 ): δ1.15(s, 3H), 1.40(t, 2H), 1.59(s, 3H), 1.66(s, 3H), 1.90(m, 2H), 2.36(d, 2H), 5.08(t, 1H), 5.86-4.96(m, 3H), 9.70(t, 1H); 13 C NMR (CDCl 3 ): 202.5, 144.7, 131.1, 123.8, 112.7, 52.6, 41.0, 38.6, 25.3, 22.3, 17.2ppm; MS (m / e): 180 (M ...

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Abstract

The present invention relates to synthesis process of 4-(1, 5-dimethyl-1-vinyl-4-hexenyl) phenol, normally named as antifeedant, and the synthesis process is superior to available ones. The synthesis process has geraniol as main material and includes the reaction with vinyl ethyl ether, Claisen rearrangement reaction to obtain 3-vinyl-rhodinal, reaction with hexahydropyridine, enamiation, conjugate addition with methyl vinyl ketone and cyclization and condensation to 4-(1, 5-dimethyl-1-vinyl-4-hexenyl)-2-cyclohexene ketone, and dehydrogenation to obtain the product 4-(1, 5-dimethyl-1-vinyl-4-hexenyl) phenol. The present invention uses natural product as main material, and has simple reaction process, high selectivity and high yield.

Description

technical field [0001] The invention relates to a synthesis method of 4-(1,5-dimethyl-1-vinyl-4-hexenyl)phenol. Background technique [0002] 4-(1,5-Dimethyl-1-vinyl-4-hexenyl)phenol, also known as the antifeedant (+)-Sporochnol, was isolated and identified from Caribbean seaweed by Shen et al. in 1993. Terpenoid phenols, experiments have shown that this natural product has significant antifeedant activity on herbivorous fish. At present, the synthesis of this substance has been reported, and the literature (Enantiomer 1997, 2, 297; Tetrahedron: Asymmetry 1999, 10, 1153; J.Chem.Res. 2000, 530; TetrahedronLetters 2002, 43, 4641) on 4- The chemical synthesis of (1,5-dimethyl-1-vinyl-4-hexenyl)phenol has been reported in detail, but the synthetic methods provided in these documents have many synthetic steps, mostly within 5 to 15 Between steps, the reaction conditions are complicated, the reagents used are expensive, and the yield is also low. Contents of the invention [...

Claims

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Application Information

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IPC IPC(8): C07C37/20C07C39/19
Inventor 哈成勇单绍军金建忠沈敏敏
Owner GUANGZHOU INST OF GEOCHEMISTRY - CHINESE ACAD OF SCI
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