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Novel method for synthesizing leaf alcohol

A technology for synthesizing leaf alcohol and a new method, which is applied in chemical instruments and methods, preparation of organic compounds, preparation of hydroxyl compounds, etc., can solve the problems of complex process and many synthesis steps, and achieve cheap raw materials, short reaction time and convenient raw materials Easy to get effect

Inactive Publication Date: 2010-11-03
SHANGHAI MARITIME UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] The purpose of the present invention is to provide a new method for the synthesis of leaf alcohol in order to overcome the defects of the existing method for synthesizing leaf alcohol, such as many synthetic steps and complex processes, and to obtain cheap 1-pentene, formaldehyde, and paraformaldehyde. , one of paraformaldehyde or formalin as raw material, through Lewis acid catalysis, one-step reaction to prepare leaf alcohol, the method is simple and easy

Method used

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  • Novel method for synthesizing leaf alcohol

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Effect test

Embodiment 1

[0021] Dissolve paraformaldehyde (3g, 0.1mol) and aluminum trichloride (0.27g, 0.002mol) in dichloromethane (20ml), start magnetic stirring, at -40°C with 1-2 drops every two seconds 1-Pentene (3.5 g, 0.05 mol) was slowly added dropwise, and after the dropwise addition was completed, the temperature was raised to room temperature, and stirring was continued for 1 hour. with saturated NaHCO 3 solution (10ml) was washed, the organic phase was dried with anhydrous sodium sulfate, dichloromethane was distilled off, and the remaining crude product was distilled under reduced pressure to obtain a mixture of leaf alcohol and trans-3-hexen-1-ol. The yield 72%. Trans-3-hexen-1-ol also exists in green plants and also has the natural fragrance of grass, so this mixture can be directly used as a spice. The mixture was rectified to obtain leaf alcohol with a yield of 36%.

Embodiment 2

[0023] Dissolve paraformaldehyde (3g, 0.1mol) and tin tetrachloride (0.32g, 0.0012mol) in dichloromethane (20ml), start magnetic stirring, and drop 1-2 drops every two seconds at -20°C 1-Pentene (3.5 g, 0.05 mol) was slowly added dropwise, and after the dropwise addition was completed, the temperature was raised to room temperature, and stirring was continued for 4 hours. with saturated NaHCO 3 solution (10ml) was washed, the organic phase was dried with anhydrous sodium sulfate, dichloromethane was distilled off, and the remaining crude product was distilled under reduced pressure to obtain a mixture of leaf alcohol and trans-3-hexen-1-ol. The yield 85%. The mixture was rectified to obtain leaf alcohol with a yield of 43%.

Embodiment 3

[0025] Dissolve paraformaldehyde (30g, 1mol) and tin tetrachloride (3.2g, 0.012mol) in carbon tetrachloride (200ml), start magnetic stirring, and drop 1-2 drops every two seconds at -20°C 1-Pentene (42 g, 0.6 mol) was added dropwise at a high speed, and after the dropwise addition was completed, the temperature was raised to room temperature, and stirring was continued for 4 hours. with saturated NaHCO 3 solution (100ml), the organic phase was dried with anhydrous sodium sulfate, dichloromethane was distilled off, and the remaining crude product was distilled under reduced pressure to obtain a mixture of leaf alcohol and trans-3-hexene-1-ol. The yield 82%. The mixture was rectified to obtain leaf alcohol with a yield of 41%.

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Abstract

The invention provides a novel method for synthesizing leaf alcohol. In the method, in catalysis of lewis acid, one of formaldehyde, paraformaldehyde or trioxymethylene performs Alder Ene reaction with 1-amylene at the temperature of minus 40 and 20 DEG C, and the materials after reaction are separated, purified and refined to prepare the target compound conveniently. The method has low-price and easily obtained raw materials, and is particularly applied to industrialized production.

Description

technical field [0001] The invention relates to a new method for synthesizing leaf alcohol. Background technique [0002] Leaf alcohol (the chemical name is cis-3-hexen-1-ol) is a very important spice. It has the natural fragrance of fresh leaves and grass. The fragrance is fresh and natural, and it is suitable for direct use as spices. Leaf alcohol and its derivatives are one of the world's most popular fragrance-type precious spices, and they have also become a symbol of the green revolution in the world's spice industry. Leaf alcohol and its esters are also indispensable flavoring substances in the production of flavors. Currently, at least 40 synthetic flavors and flavors contain leaf alcohol. The current world demand is about 200 tons / year. [0003] Leaf alcohol is present in many green plants. However, due to the low boiling point and high water solubility, the production of naturally extracted leaf alcohol is extremely small and the production cost is high. At pres...

Claims

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Application Information

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IPC IPC(8): C07C33/025C07C29/38
Inventor 王军华朱梅芳王建华任洪敏董丽华
Owner SHANGHAI MARITIME UNIVERSITY
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