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Preparation method for substituted cinnamyl alcohol

A technology of cinnamyl alcohol and cinnamaldehyde, which is used in pharmaceutical chemical intermediates and related chemical fields, can solve the problems of high price, non-reusable, difficult separation and recovery, etc., and achieves the effects of good reproducibility and high selectivity

Active Publication Date: 2015-04-08
DALIAN UNIV OF TECH
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  • Abstract
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AI Technical Summary

Problems solved by technology

[0003] The traditional method for preparing cinnamyl alcohol is mainly divided into two categories, one is a homogeneous catalyst combined with Ru, Ir and other transition metals and ligands, this type of catalyst has high activity and selectivity, however these transition metals and ligands It has the disadvantages of high price, difficulty in separation and recovery, and non-reusability [OHKUMA T, OOKA H, IKARIYA T, et al. Preferential hydrogenation of aldehydes and ketones. J. Am. Chem. Soc., 1995, 117 (41): 10417 -10418; WU X, LIU J, LI X, et al.On water and in air:fast and highly chemoselective transfer hydrogenation of aldehydes with iridium catalysts.Angew.Chem.Int.Ed.,2006,45(40):6718 -6722.]; The second is heterogeneous catalysts that have been studied more. The factors affecting the catalytic effect of this type of catalyst are more complicated, mainly including catalyst active components, additives, carriers and different reduction methods, etc., and the load is in The heterogeneous catalysts on metal oxides will be deactivated by the aggregation of metal nanoparticles after repeated recycling [BUS E, PRINS R, VAN BOKHOVEN J A. Origin of the cluster-size effect in the Hydrogenation of cinnamaldehyde over supported Au catalysts.Catalysis Communications,2007,8(9):1397-1402; LIU L,QIAO B,MA Y,et al.Ferric hydroxide supported gold subnano clusters or quantum dots:enhanced catalytic hydrogenation performance in chemo .Dalton transactions,2008,19:2542-2548.]

Method used

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  • Preparation method for substituted cinnamyl alcohol
  • Preparation method for substituted cinnamyl alcohol
  • Preparation method for substituted cinnamyl alcohol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1: the synthesis of α-methylcinnamyl alcohol

[0024] In the methanol (5mL) solvent that adds AuNPore (10.0mg, 10mol%) catalyst, add substrate α-methylcinnamaldehyde (74.07mg, 0.5mmol), sodium hydroxide (200mg, 5mmol) and triisopropyl Silane (791.8mg, 5.0mmol), placed on a magnetic stirrer at 50°C for 24h, column chromatography (silica gel, 200-300 mesh; developer, petroleum ether: ethyl acetate = 20:1) to obtain α-formazan Cinnamyl alcohol 45.91mg, yield 62%.

[0025]

[0026] yellow liquid; 1 H NMR (CDCl 3 ,400MHz)δ:7.32(d,J=7.6Hz,2H),7.27(d,J=7.2Hz,2H),7.23–7.20(m,1H),6.52(s,1H),4.17(s,2H ),1.99(br s,1H,OH),1.89(s,3H).

Embodiment 2

[0027] Embodiment 2: the synthesis of α-methylcinnamyl alcohol

[0028] In the methanol (5mL) solvent that adds AuNPore (10.0mg, 10mol%) catalyst, add substrate α-methylcinnamaldehyde (74.07mg, 0.5mmol), potassium hydroxide (280mg, 5mmol) and triisopropyl Silane (791.8mg, 5.0mmol), placed on a magnetic stirrer at 60°C for 24h, column chromatography (silica gel, 200-300 mesh; developer, petroleum ether: ethyl acetate = 20:1) to obtain α-formazan 48.13 mg of cinnamyl alcohol, yield 65%.

[0029]

[0030] yellow liquid; 1 H NMR (CDCl 3 ,400MHz)δ:7.32(d,J=7.6Hz,2H),7.27(d,J=7.2Hz,2H),7.23–7.20(m,1H),6.52(s,1H),4.17(s,2H ),1.99(br s,1H,OH),1.89(s,3H).

Embodiment 3

[0031] Embodiment 3: the synthesis of 4-methylcinnamyl alcohol

[0032] In the acetone (5mL) solvent that adds AuNPore (10.0mg, 10mol%) catalyst, add substrate 4-methylcinnamaldehyde (74.07mg, 0.5mmol), sodium hydroxide (200mg, 5mmol) and triisopropyl Silane (791.8mg, 5.0mmol), placed on a magnetic stirrer at 50°C for 24h, column chromatography (silica gel, 200-300 mesh; developer, petroleum ether: ethyl acetate = 20:1) to obtain 4-formazan 45.91 mg of cinnamyl alcohol, yield 70%.

[0033]

[0034] colorless solid; 1 H NMR (CDCl 3,400MHz)δ:7.32(d,J=8.0Hz,2H),7.16(d,J=8.0Hz,2H),6.62(d,J=16.0Hz,1H),6.35(dt,J=16.0,4.0 Hz, 1H), 4.33(dd, J=4.0, 2.0Hz, 2H), 2.38(s, 3H), 1.94(br s, 1H, OH); m.p., 50–52℃.

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Abstract

Belonging to the field of pharmaceutical and chemical intermediates and related chemical technologies, the invention relates to a preparation method for substituted cinnamyl alcohol. The method provided by the invention adopts cinnamic aldehyde and its derivative as raw materials, takes a nano-porous gold catalyst as the catalyst, and employs organosilane as the hydrogen source and alkali as the additive to prepare substituted cinnamyl alcohol by selective hydrogenation. Specifically, the cinnamic aldehyde and its derivative and the hydrogen source are in a mole ratio of 1:0.1-1:15, the cinnamic aldehyde and its derivative and the alkali are in a mole ratio of 1:0.1-1:15, and the mole concentration of the cinnamic aldehyde and its derivative in a solvent is 0.01mmol / mL-2mmol / mL. According to the invention, the product has high selectivity, the catalyst has good reproducibility, and the catalytic effect is not significantly reduced after repeated use, thus providing possibility for realization of industrialization.

Description

technical field [0001] The invention belongs to the field of pharmaceutical and chemical intermediates and related chemical technologies, and relates to a preparation method for substituted cinnamyl alcohol. Background technique [0002] Cinnamyl alcohol is used as a flavor and fragrance, mainly used in the preparation of fruit flavors, cosmetic flavors and soap flavors, and is also used as a fixative because of its long-lasting and mild aroma. At the same time, cinnamyl alcohol is a synthetic raw material for the synthesis of cardiovascular and cerebrovascular drugs, which can effectively inhibit lung tumors caused by viruses. It is clinically used for blood cancer, esophageal cancer and other diseases, and has broad market prospects. [0003] The traditional method for preparing cinnamyl alcohol is mainly divided into two categories, one is a homogeneous catalyst combined with Ru, Ir and other transition metals and ligands, this type of catalyst has high activity and selec...

Claims

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Application Information

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IPC IPC(8): C07C29/14C07C33/30C07C33/48C07C41/26C07C43/253
CPCC07C29/14C07C41/26C07C33/30C07C33/483C07C43/23
Inventor 冯秀娟巴拉拉姆·塔卡勒包明于晓强王善强
Owner DALIAN UNIV OF TECH
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