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Synthesis method of chiral compound R-(+)-2-methyl-3-phenyl-1-propyl alcohol

A technology for chiral compounds and synthesis methods, applied in the field of chiral compound synthesis, can solve problems such as no further research, and achieve the effect of ensuring achievability

Active Publication Date: 2019-03-22
江苏广域化学有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are only very few academic literatures that involve the synthesis of the compound (±)-2-methyl-3-phenyl-1-propanol; but these literatures have not been further studied, and a single chiral Isomer R-(+)-2-methyl-3-phenyl-1-propanol

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Step 1: Using α-methylcinnamaldehyde as a raw material, add an appropriate catalyst, and carry out catalytic hydrogenation with hydrogen at a certain temperature and pressure to obtain (±)-2-methyl-3-phenyl-1-propane alcohol.

[0054] 110 g of α-methylcinnamaldehyde and 550 g of isopropanol were added to a 2 L stainless steel autoclave, and after nitrogen replacement, 1.1 g of palladium carbon was added under nitrogen protection. Then nitrogen replacement three times, hydrogen replacement three times; first keep warm at 50°C-70°C, continuously feed 0.4MPa hydrogen, stir and react for 5 hours; then keep warm at 130°C-150°C, continue to feed 0.6MPa hydrogen, stir for 5 hours. After stopping the reaction, lowering the temperature, and replacing with nitrogen three times, the reaction liquid was taken out and filtered, and the filtrate was concentrated to obtain 111 g of (±)-2-methyl-3-phenyl-1-propanol, with a gas chromatography purity of ≥95%.

[0055] Step 2: Use (±)-2-...

Embodiment 2

[0065] Step 1: Using α-methylcinnamaldehyde as a raw material, add an appropriate catalyst, and carry out catalytic hydrogenation with hydrogen at a certain temperature and pressure to obtain (±)-2-methyl-3-phenyl-1-propane alcohol.

[0066] Add 800 g of α-methylcinnamaldehyde in a 2L stainless steel autoclave without solvent. After nitrogen replacement, 0.8 g of platinum carbon was added under nitrogen protection. Then replace three times with nitrogen, three times with hydrogen, keep warm at 0°C-20°C and continuously feed 5MPa hydrogen, stir and react for 72 hours. Stop the reaction, replace with nitrogen three times, take out the reaction liquid and filter, and concentrate the filtrate to obtain 813 g of (±)-2-methyl-3-phenyl-1-propanol, with gas chromatography purity ≥ 99%.

[0067] Step 2: Use (±)-2-methyl-3-phenyl-1-propanol as raw material, add a certain amount of solvent, catalyst and phthalic anhydride, heat up to carry out esterification reaction; after a certain p...

Embodiment 3

[0077] Step 1: Using α-methylcinnamaldehyde as a raw material, add an appropriate catalyst, and carry out catalytic hydrogenation with hydrogen at a certain temperature and pressure to obtain (±)-2-methyl-3-phenyl-1-propane alcohol.

[0078] 55g of α-methylcinnamaldehyde and 550g of tetrahydrofuran were added to a 2L stainless steel autoclave, and after nitrogen replacement, 22.0g of Raney nickel was added under nitrogen protection. Then replace three times with nitrogen, three times with hydrogen, keep warm at 50°C-70°C and continuously feed 0.1MPa hydrogen, stir and react for 20 hours. After stopping the reaction, lowering the temperature, and replacing with nitrogen three times, the reaction solution was taken out and filtered, and the filtrate was concentrated to obtain 56 g of (±)-2-methyl-3-phenyl-1-propanol, with a gas chromatography purity of ≥97%.

[0079] Step 2: Use (±)-2-methyl-3-phenyl-1-propanol as raw material, add a certain amount of solvent, catalyst and phth...

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PUM

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Abstract

The invention discloses a synthesis method of a chiral compound R-(+)-2-methyl-3-phenyl-1-propyl alcohol. The synthesis method comprises the following steps: taking alpha-methyl cinnamaldehyde as a raw material and performing a catalytic hydrogenation reaction on the alpha-methyl cinnamaldehyde to obtain (plus or minus)-2-methyl-3-phenyl-1-propyl alcohol; performing an esterification reaction on the (plus or minus)-2-methyl-3-phenyl-1-propyl alcohol and phthalic anhydride to form monoester; performing an acid-base reaction on the monoester and S-(-)-alpha-phenylethylamine to form salt; separating and purifying a single chiral isomer in the salt through crystallization and recrystallization; performing a hydrolysis reaction to obtain R-(+)-2-methyl-3-phenyl-1-propyl alcohol and a hydrolysisby-product; and finally, removing the hydrolysis by-product through separation and purification to obtain the R-(+)-2-methyl-3-phenyl-1-propyl alcohol.

Description

technical field [0001] The invention relates to the field of chiral compound synthesis, in particular to a synthesis method of the chiral compound R-(+)-2-methyl-3-phenyl-1-propanol. Background technique [0002] Chiral alcohols are important intermediates for the synthesis of chiral liquid crystal monomers, chiral drugs and alkaloid chiral chemicals. [0003] The method of obtaining unnatural chiral alcohol compounds is generally to first synthesize them by chemical methods; however, after chemical synthesis, only two kinds of mixtures of opposite chirality and isomers (commonly known as racemic mixture). Therefore, after chemical synthesis, the separation and purification of two chiral isomers are often required. [0004] The separation and purification methods of chiral isomers mainly include chemical resolution, chromatography and extraction. Chromatography has a small amount of processing, low efficiency, and cannot be industrialized, so that the practicability is gr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C29/09C07C33/20C07C29/92C07C29/141
CPCC07B2200/07C07C29/095C07C29/141C07C29/92C07C33/20
Inventor 刁伯真张立猛康杰
Owner 江苏广域化学有限公司
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