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A kind of method of synthesizing unsaturated primary alcohol

An unsaturated and primary alcohol technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve problems such as a large number of wastes, potential safety hazards, environmental pollution, etc., and achieve low reaction temperature, broad development prospects, and choice good effect

Active Publication Date: 2021-08-03
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In the traditional method, high temperature and high pressure hydrogenation is used, inorganic reducing agents such as sodium borohydride are added, or formic acid and sodium formate are used to prepare unsaturated primary alcohols. These methods have potential safety hazards, poor selectivity and a large amount of waste, which is harmful to the environment. also cause some pollution

Method used

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  • A kind of method of synthesizing unsaturated primary alcohol
  • A kind of method of synthesizing unsaturated primary alcohol
  • A kind of method of synthesizing unsaturated primary alcohol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1: cinnamyl alcohol

[0025] 3-Phenylprop-2-en-1-ol

[0026]

[0027] Cinnamaldehyde (132mg, 1.0mmol), cat.[Ir] (1.1mg, 0.002mmol, 0.2mol%) and isopropanol (5mL) were sequentially added to a 25mL Kirschner tube, N 2 Protected and reacted at 120°C for 12h. Cool to room temperature, remove solvent by rotary evaporation, then obtain pure target compound by column chromatography (developing solvent: sherwood oil / ethyl acetate), productive rate: 92%

[0028] 1 H NMR (500MHz, CDCl 3 )δ7.36(d, J=7.8Hz, 2H), 7.29(t, J=7.6Hz, 2H), 7.22(t, J=7.3Hz, 1H), 6.59(d, J=16.0Hz, 1H) ,6.33(dt,J=15.9and 5.7Hz,1H),4.28(d,J=5.7Hz,2H),2.34(br s,1H); 13 C NMR (125MHz, CDCl 3 ) δ 136.6, 130.9, 128.5, 128.4, 127.6, 126.4, 63.5.

Embodiment 2

[0029] Embodiment 2: 3-methylcinnamyl alcohol

[0030] 3-M-tolylprop-2-en-1-ol

[0031]

[0032] 3-Methylcinnamaldehyde (146mg, 1.0mmol), cat.[Ir] (1.1mg, 0.002mmol, 0.2mol%) and isopropanol (5mL) were sequentially added to a 25mL Kirschner tube, N 2 Protection, reaction at 100°C for 12h. Cool to room temperature, remove solvent by rotary evaporation, then obtain pure target compound by column chromatography (developing solvent: sherwood oil / ethyl acetate), productive rate: 96%

[0033] 1 H NMR (500MHz, CDCl 3 )δ7.23-7.19(m,3H),7.07(d,J=6.6Hz,1H),6.60(d,J=15.9Hz,1H),6.36(dt,J=15.9and 5.8Hz,1H), 4.33(d, J=5.6Hz, 2H), 2.35(s, 3H); 13 C NMR (125MHz, CDCl 3 ) δ 138.1, 136.6, 131.2, 128.4, 128.3, 127.2, 123.6, 63.6, 21.3.

Embodiment 3

[0034] Embodiment 3: 2-methoxycinnamyl alcohol

[0035] 3-(2-Methoxyphenyl)prop-2-en-1-ol

[0036]

[0037] 2-Methoxycinnamaldehyde (162mg, 1.0mmol), cat.[Ir] (1.1mg, 0.002mmol, 0.2mol%) and isopropanol (5mL) were sequentially added to a 25mL Kirschner tube, N 2 Protected and reacted at 120°C for 12h. Cool to room temperature, remove solvent by rotary evaporation, then obtain pure target compound by column chromatography (developing solvent: sherwood oil / ethyl acetate), productive rate: 94%

[0038] 1 H NMR (500MHz, CDCl 3 )δ7.43(d, J=7.6Hz, 1H), 7.24-7.21(m, 1H), 6.92(t, J=7.5Hz, 2H), 6.87(d, J=8.2Hz, 1H), 6.38( dt, J=16.1 and 5.9Hz, 1H), 4.32(d, J=5.9Hz, 2H), 3.84(s, 3H), 1.83(br s, 1H); 13 C NMR (125MHz, CDCl 3 ) δ 156.7, 129.2, 128.7, 126.9, 126.1, 125.7, 120.6, 110.8, 64.1, 55.4.

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Abstract

The invention discloses a method for synthesizing unsaturated primary alcohol. In a reaction vessel, add unsaturated aldehyde, transition metal catalyst iridium complex and isopropanol; the reaction mixture is heated in an oil bath, and after several hours of reaction, it is cooled After reaching room temperature, the solvent was removed by rotary evaporation, and then separated by column to obtain the target compound. The invention uses unsaturated aldehyde as raw material, uses isopropanol as hydrogen source and solvent, and generates unsaturated primary alcohol through hydrogen transfer under the participation of transition metal iridium catalyst. The reaction exhibits three remarkable advantages: 1) low reaction temperature; 2) use of cheap, safe, and nontoxic isopropanol; 3) low catalyst consumption and high reaction atom economy; 4) good selectivity. Therefore, this reaction meets the requirements of green chemistry and has broad development prospects.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis chemistry, and in particular relates to a method for synthesizing unsaturated primary alcohols. Background technique [0002] Unsaturated primary alcohols are an important class of organic compounds, not only important pharmaceutical intermediates, but also widely used in spices, food and so on. (a) M.C. Pirrung, Chem. Eur. J. 2006, 12, 1312–1317; (b) S. Kobayashi, K. Manabe, Acc. Chem. Res. 2002, 35, 209-217; (c) C. I. Herrerias, X. Q. Yao, Z.P.Li, C.J.Li, Chem.Rev.2007, 107, 2546-2562; (d) F.Joo, Acc.Chem.Res. 2002, 35, 738–745; (e) X.F.Wu, J.L.Xiao, Chem. Commun.2007, 2449-2466; [0003] In the traditional method, high temperature and high pressure hydrogenation is used, inorganic reducing agents such as sodium borohydride are added, or formic acid and sodium formate are used to prepare unsaturated primary alcohols. These methods have potential safety hazards, poor selectivity and a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C33/32C07C29/14C07C43/23C07C41/26C07C33/48C07C205/19C07C201/12C07C33/28C07D307/42C07C33/03C07C33/14C07C33/12C07C33/02
CPCC07C29/14C07C41/26C07C201/12C07D307/42C07C33/32C07C43/23C07C33/483C07C205/19C07C33/28C07C33/03C07C33/14C07C33/12C07C33/02
Inventor 李峰王荣周
Owner NANJING UNIV OF SCI & TECH