LU505773B1 - A base catalyzed method for preparing substituted propargyl alcohol from paraformaldehyde and alkyne - Google Patents

A base catalyzed method for preparing substituted propargyl alcohol from paraformaldehyde and alkyne Download PDF

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LU505773B1
LU505773B1 LU505773A LU505773A LU505773B1 LU 505773 B1 LU505773 B1 LU 505773B1 LU 505773 A LU505773 A LU 505773A LU 505773 A LU505773 A LU 505773A LU 505773 B1 LU505773 B1 LU 505773B1
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preparation
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paraformaldehyde
tba
propargyl alcohol
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Yabin Wang
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Univ Yanan
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
    • C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
    • C07C29/42—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing triple carbon-to-carbon bonds, e.g. with metal-alkynes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
    • C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
    • C07C29/86—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by liquid-liquid treatment
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/34—Separation; Purification; Stabilisation; Use of additives
    • C07C41/38—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment

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  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention provides an efficient preparation method for preparing substituted propargyl alcohol by using phenylacetylene compounds and paraformaldehyde through the action of alkali catalyst. The main steps are to add phenylacetylene compounds and paraformaldehyde to the corresponding solvent, add alkali catalyst under stirring conditions, heat the reaction for several hours, add water to quench the reaction, then use ethyl acetate to extract, dry, concentrate and purify the solution to obtain the product. The preparation and synthesis method has the advantages of simple and effective operation, mild reaction conditions and high yield, which can well solve the technical problem of high cost of the current preparation route of substituted propargyl alcohol intermediate.

Description

A BASE CATALYZED METHOD FOR PREPARING SUBSTITUTED PROPARGYL ALCOHOL
FROM PARAFORMALDEHYDE AND ALKYNE
TECHNICAL FIELD
The invention belongs to the field of medicinal chemical intermediates, in particular to a synthesis method for efficiently preparing substituted propargyl alcohol by base catalysis.
BACKGROUND
Substituted propargyl alcohol is an important organic and pharmaceutical intermediate, which can carry out a variety of chemical conversion reactions. At present, the main aryl propargylic alcohols in the market are few and expensive, which is not conducive to the further healthy development of organic chemistry and medicine. There are usually two kinds of traditional methods to prepare substituted propargyl alcohol: (1) equivalent base or strong base promoted addition reaction; (2) By palladium catalyzed Sonogashira coupling reaction. In these two kinds of methods, there are some shortcomings, such as using equivalent base or organometallic strong base, easy ignition, expensive palladium catalyst, etc. the preparation method has potential safety hazards and high costs, does not meet the requirements of green chemistry, and is not conducive to the reaction scale-up production. Therefore, it is necessary to develop green and efficient synthetic methods of substituted propargylic alcohols, which are simple to operate, easy to scale up, and safe and reliable, to solve the adverse situation of serious shortage and high price of important pharmaceutical intermediates such as different substituted propargylic alcohols in the market.
SUMMARY OF THE INVENTION
In view of the shortcomings and drawbacks in the existing technology, the present invention has found through experimental exploration that, under mild conditions, some bases can catalyze the efficient addition reaction of paraformaldehyde and alkynes, which can be successfully converted into substituted propargylic alcohols. According to this, an efficient synthesis method of base catalyzed preparation of substituted propargylic alcohols from paraformaldehyde and alkynes is provided, thereby developing a greener synthesis technology route, and the method uses a catalytic amount of base Simple operation, mild reaction conditions, safe and reliable, easy to scale up.
The technical scheme provided by the invention is as follows: 17905773
A method for preparing substituted propargyl alcohol from paraformaldehyde and alkyne catalyzed by base, which is characterized by comprising the following steps: 1) The phenylacetylene compounds and paraformaldehyde were added into the corresponding solvent DMSO according to the molar ratio of 1:1.5 to make the solute concentration of phenylacetylene compounds reach 0.5mol/L; 2) Under stirring conditions, add basic catalyst, the amount of which is 10% of the molar amount of phenylacetylene compound according to the base equivalent it can provide; 3) The reaction was quenched by adding water after heating to 25-60 °C for 2-24 hours; 4) The product was extracted with ethyl acetate, dried, concentrated and purified after liquid separation;
The reaction formula for preparing substituted propargyl alcohol from phenylacetylene compounds and paraformaldehyde is as follows: a HOH ad. J + EE a i HUIT £ D
The number of R substituents can be 0-5.
Preferably, the type of the R substituent can be selected from one or more of F, Br, CI, |,
CN, CO.Et, CO,Me, Ac, ArCO, CF3, NO», C1-8 alkyl, C1-8 alkoxy, Et, n-Pr, i-Pr, Bu,
CH,=CH, OMe, OEt, OPr; Further, the R substituent can be selected from one or more of F, Br,
Cl, I, CN, COzEt, CO,Me, Ac, ArCO, CFs, NO>; Or further, the R substituent can be selected from one or more of Me, Et, n-Pr, i-Pr, Bu, CH=CH, OMe, OEt, OPr.
Preferably, the stirring rate of step 2) is 200-500r/min, further, the stirring rate of step 2) is 300r/min.
Preferably, the heating temperature in step 3) is 40-60 °C, further, the heating temperature in step 4) can be 40 C or 60 °C.
Preferably, the alkaline catalyst can be KOH, NaOH, K2CO3, Cs;COs, tetrabutylammonium hydroxide (TBA-OH), tetraethyl ammonium hydroxide (TEA-OH), tetramethyl ammonium hydroxide (TMA-OH), and further TBA-OH can be selected.
The preparation method of substituted propargyl alcohol proposed by the invention has the 0°77 following beneficial effects: 1.It greatly reduces the amount of basic catalyst used in the traditional method of preparing substituted propargyl alcohol, and overcomes the disadvantage of high cost of palladium catalyst. 2.The reaction conditions are mild, the required heating temperature is low, and the reactions involved in the synthesis of the target compounds have simple synthesis steps, few side reactions, good product yield, short time consumption, simple operation, easy amplification, good safety and reliability, which can greatly reduce the technical cost of preparing substituted propargyl alcohol pharmaceutical intermediates in industrial production.
DESCRIPTION OF DRAWINGS
Figure 1 is the H-NMR of the product 3aa from example 1 (400MHz in CDCIs)
Figure 2 is the 3C-NMR of the product 3aa from example 1 (400MHz in CDCls)
Figure 3 is the H-NMR of the product 3ab of example 2 (400MHz in CDCIs)
Fig. 4 is the 3C-NMR (400MHz in CDCIs) of the product 3ab of example 2
Figure 5 is the *H-NMR of the product 3ac of example 3 (400MHz in CDCIs)
Figure 6 shows the 3C-NMR of the product 3ac from example 3 (400MHz in CDCls)
Figure 7 shows the H-NMR of the product 3ad of example 4 (400MHz in CDCIs)
Figure 8 is the 3C-NMR of the product 3ad of example 4 (400MHz in CDCIs)
Figure 9 is the *H-NMR of the product 3ae of example 5 (400MHz in CDCIs)
Figure 10 is the 3C-NMR of the product 3ae of example 5 (400MHz in CDCIs)
Figure 11 shows the H-NMR of the product 3af of example 6 (400MHz in CDCIs)
Figure 12 is the 13C-NMR of the product 3af of example 6 (400MHz in CDCls)
Figure 13 shows that the experimenter was adjusting the heating temperature during the amplification reaction of examples 1-1.
DETAILED DESCRIPTION OF THE INVENTION
The selection of reaction parameters and conditions of examples 1-6 given by the invention is based on the reactant raw materials of example 1, and is obtained by setting different alkali types, solvent conditions and heating temperatures, as shown in Table 1. The separation yields of examples 1-6 are higher than 60%, indicating that the synthesis method of base catalyzed paraformaldehyde and phenylacetylene compounds to prepare substituted propargyl alcohol obtained by the invention is very efficient and has great commercial value. 17905773
Example 1
The specific preparation method of compound 3-phenyl-2-propyn-1-ol (3aa) is as follows:
Phenylacetylene (1.0 mmol) and paraformaldehyde (1.5 mmol) were added to the corresponding solvent DMSO (0.5 mol/L), and alkali tetrabutylammonium hydroxide (TBA-OH) (0.1 equiv) was added under stirring to catalyze the reaction. Without inert gas protection, the reaction was heated at 60 °C under air for 10 hours. After TLC inspection until the reaction was complete, 10 ml of water was added to quench the reaction, extracted with ethyl acetate (10ml*3), separated, dried and concentrated to obtain the crude product. After the crude product was dissolved in 1.0mI
CDCIs, ethylene glycol dimethyl ether was quantitatively added as the internal standard, and the yield of 3aa NMR was determined to be 99%, and the yield of column chromatography was 93%.
Its structural formula is as follows: > 3aa NMR data were as follows: *H NMR (400 MHz, CDCls-d) & 7.55-7.37 (m, 2H), 7.36-7.22 (m, 3H), 4.49 (s, 2H), 2.96 (s, 1H) ppm, as shown in Figure 1; 3C NMR (100 MHz, CDCls-d) & 131.80, 128.59, 128.58, 122.67, 87.47, 85.64, 51.51 ppm; As shown in Figure 2.
Example 1-1 (amplification reaction)
The reaction of compound 3-phenyl-2-propyn-1-ol (3aa) was amplified. The specific preparation method was as follows:
Phenylacetylene (200 mmol) and paraformaldehyde (300 mmol) were added to the corresponding solvent DMSO (0.5 mol/L), and the base tetrabutylammonium hydroxide (TBA-OH) (0.1 equiv.) was added under stirring to catalyze the reaction. Without the protection of inert gas, the reaction was heated at 60 °C under air for 10 hours. As shown in Figure 13, after TLC inspection until the reaction was complete, 200 ml of water was added to quench the reaction, extracted with ethyl acetate (150mli*3), dried and concentrated after liquid separation, The crude product was obtained, and the product 3aa (22.47g, separation yield 85%) was obtained by column chromatography.
Example 2 LU505773
The specific preparation method of compound 3- (4-chlorophenyl) - 2-propargyl-1-ol (3- (4- chlorophenyl) prop-2-yn-1-ol) (3ab) is as follows:
Add 1.0 mmol of 4-chlorophenylacetylene and paraformaldehyde (1.5 mmol) to the 5 corresponding solvent DMSO (0.5 mol/l), add alkali TBA-OH (0.1 equivalent) to catalyze the reaction under stirring, and heat the reaction at 60 °C under air for 10 hours without inert gas protection.
After TLC inspection until the reaction is complete, add 10ml of water to quench the reaction, extract with ethyl acetate (10ml*3), dry and concentrate after liquid separation, and then separate by column chromatography to obtain the pure product 3ab, The separation yield was 68%. oa cl 3ab NMR data were as follows: *H NMR (400 MHz, CDCls-d) & 7.37-7.32 (m, 2H), 7.29-7.25 (m, 2H), 4.48 (s, 2H) ppm, as shown in Figure 3; 3C NMR (100 MHz, CDCls-d) 5 134.66, 133.01, 128.78, 121.07, 88.21, 84.70, 51.68 ppm, as shown in Figure 4.
Example 3
The specific preparation method of compound 3- (4-fluorophenyl) - 2-propyne-1-ol (3- (4- fluorophenyl) prop-2-yn-1-ol) (3ac) is as follows:
Add 1.0 mmol of 4-fluorophenylacetylene and 1.5 mmol of paraformaldehyde to the corresponding solvent DMSO (0.5 mol/L), add alkali TBA-OH (0.1 equiv.) to catalyze the reaction under stirring, and heat the reaction at 60 °C in air for 10 hours without inert gas protection. After
TLC inspection until the reaction is complete, add 10ml of water to quench the reaction, extract with ethyl acetate (10ml*3), dry and concentrate after liquid separation, and then separate by column chromatography to obtain the pure product 3ac, The separation yield was 81%.
Oo
F
3ac NMR data were as follows: 'H NMR (400 MHz, CDCls-d) & 7.44-7.30 (m, 2H), 7.01-6.87 (m 905773 2H), 4.46 (s, 2H), 3.38 (s, 1H) ppm, as shown in Figure 5; 13C NMR (101 MHz, CDCls-d) 6 162.63 (d, J = 250.8 Hz), 133.68 (d, J = 8.1 Hz), 118.70 (d, J = 4.0 Hz), 115.78 (d, J = 22.1 Hz), 87.09 (d, J = 1.0 Hz), 84.56, 51.32 ppm; As shown in Figure 6.
Example 4
The specific preparation method of compound 3- (4-methoxyphenyl) - 2-propyn-1-ol (3- (4- methoxyphenyl) prop-2-yn-1-ol) (3ad) is as follows: 4-methoxyphenylacetylene (1.0 mmol) and paraformaldehyde (1.5 mmol) were added to the corresponding solvent DMSO (0.5 mol/L), and alkali TBA-OH (0.1 equiv) was added to catalyze the reaction under stirring. Without the protection of inert gas, the reaction was heated at 60 °C under air for 10 hours. After TLC inspection until the reaction was complete, 10ml of water was added to quench the reaction, and the reaction was extracted with ethyl acetate (10ml*3). The solution was separated, dried, concentrated, and separated by column chromatography to obtain the pure product 3ad with a separation yield of 64%.
OT
MeO
The 3ad NMR data were as follows: 'H NMR (400 MHz, CDClz-d) & 7.34 (d, J = 8.8 Hz, 2H), 6.79 (d, J = 8.8 Hz, 2H), 4.46 (s, 2H), 3.75 (s, 3H), 2.86 (s, 1H) ppm, as shown in Figure 7; ‘°C NMR (100
MHz, CDCls-d) 6 159.72, 133.28, 114.77, 114.02, 86.14, 85.55,55.36, 51.56 ppm, as shown in Figure 8.
Example 5
The specific preparation method of compound 3- (p-tolyl) - 2-propyne-1-ol (3- (p-tolyl) prop-2- yn-1-ol) (3ae) is as follows: 4-methylphenylacetylene 1a (1.0 mmol) and paraformaldehyde (1.5 mmol) were added to the corresponding solvent DMSO (0.5 mol/L), and alkali TBA-OH (0.1 equiv) was added to catalyze the reaction under stirring. Without the protection of inert gas, the reaction was heated at 60 °C under air for 10 hours. After TLC inspection until the reaction was complete, 10ml of water was added to quench the reaction, and the reaction was extracted with ethyl acetate (10ml*3). The solution was separated, dried, concentrated, and separated by column chromatography to obtain the oure 05773 product 3ae, with a separation yield of 78%.
GF OH oo 3ae NMR data were as follows: *H NMR (400 MHz, CDCI>-d) & 7.33 (d, J = 8.1 Hz, 2H), 7.09 (d, J = 8.4 Hz, 2H), 4.49 (s, 2H), 2.96 (s, 1H), 2.33 (s, 3H) ppm, As shown in Figure 9; ‘°C NMR (100 MHz,
CDCls-d) 6 138.69, 131.72, 129.19, 119.61, 86.79, 85.78, 51.55, 21.57 ppm, as shown in Figure 10.
Example 6
The specific preparation method of compound 3- (4-phenylethyl) - 2-propynyl-1-ol (3af) is as follows: 4-ethylphenylacetylene 1a (1.0 mmol) and paraformaldehyde 2A (1.5 mmol) were added to the corresponding solvent DMSO (0.5 mol/L), and alkali TBA-OH (0.1 equiv) was added to catalyze the reaction under stirring. Without the protection of inert gas, the reaction was heated at 60 °C under air for 10 hours. After TLC inspection, the reaction was quenched by adding 10ml of water, extracted with ethyl acetate (10ml*3), separated, dried, concentrated, and separated by column chromatography to obtain the pure product 3af, with a separation yield of 62%.
Its structural formula is as follows:
Sol C
The 3af NMR data were as follows: *H NMR (400 MHz, CDCIz-d) & 7.36 (d, J = 8.2 Hz, 2H), 7.12 (d, J = 7.9 Hz, 2H), 4.49 (s, 2H), 2.67 (s, 1H), 2.63 (q, J = 7.6 Hz, 2H), 1.21 (t, J = 7.5 Hz, 3H) ppm, As shown in Figure 11; 13C NMR (100 MHz, CDCls-d) & 144.98, 131.81, 127.99, 119.82, 86.73, 85.86, 51.63, 28.89, 15.43 ppm, as shown in Figure 12.
Optimization screening test of reaction conditions
Taking example 1 as the basic object of the test, the test parameters were adjusted according to the test parameters described in Table 1 below to explore the comparison data of NMR yield under different alkali conditions, solvent conditions and heating temperature. The test results are as follows:
Table 1 Comparison of NMR yield of 3-phenyl-2-propyn-1-ol (3aa) under different test parameters
Serial Base solvent Temperature NMR yield of number (10 mol%) (2.0 mL) /°C 3aa (%) 1 KOH DMSO (0.5mol/L) 60 56.4 2 NaOH DMSO (0.5mol/L) 60 53 3 K2CO3 DMSO (0.5mol/L) 60 69.4 4 Cs2CO3 DMSO (0.5mol/L) 60 47.8
DBU DMSO (0.5mol/L) 60 <5 6 (example 1) TBA-OH DMSO (0.5mol/L) 60 99 (93) a 7 EtsN DMSO (0.5mol/L) 60 No Reaction 8 Na,COs DMSO (0.5mol/L) 60 No Reaction 9 TBA-OH EtOH (0.5mol/L) 60 No Reaction
TBA-OH H20 (0.5mol/L) 60 No Reaction 11 TBA-OH THF (0.5mol/L) 60 15 12 TBA-OH CH3CN ((0.5mol/L) 60 21 13 TBA-OH DMF (0.5mol/L) 60 36 14 TBA-OH Dioxane (0.5mol/L) 60 10
TBA-OH DMSO (0.5mol/L) 25 90.8 16 TBA-OH DMSO (0.5mol/L) 40 97.8 17° TBA-OH DMSO (0.5mol/L) 60 98 18° TBA-OH DMSO (0.5mol/L) 60 88 19% TBA-OH DMSO (0.5mol/L) 60 85 20° nothing DMSO (0.5mol/L) 60 <5 a is the isolated yield; P reacts under nitrogen protection;® Use 5%TBA-OH;* Use 2.5%TBA-OH; € do not use TBA-OH.
According to the comparison results of the above tests, DMSO is the solvent, TBA-OH is the 5 base catalyst, and the temperature is 60 °C. Under this reaction condition, the product generation rate of this kind of reaction is the best. According to the test data, the parameter setting of the synthesis method in the invention is not to select the conventional alkali type, conventional solvent, or set the conventional temperature conditions to realize the invention intent.
It should be understood that although the description is described according to the 10 embodiment, this description of the description is only for clarity. Those skilled in the art should take the description as a whole to form other embodiments that can be understood by those skilled in the art, which should also belong to the protection scope of the invention.

Claims (10)

1. A method for preparing substituted propargyl alcohol from paraformaldehyde and alkyne catalyzed by base, which is characterized by comprising the following steps: 1) the phenylacetylene compounds and paraformaldehyde were added into the corresponding solvent dmso according to the molar ratio of 1:1.5 to make the solute concentration of phenylacetylene compounds reach 0.5mol/I; 2) under stirring conditions, add basic catalyst, the amount of which is 10% of the molar amount of phenylacetylene compound according to the base equivalent it can provide; 3) the reaction was quenched by adding water after heating to 25-60 °C for 2-24 hours; 4) the product was extracted with ethyl acetate, dried, concentrated and purified after liquid separation; The reaction formula for preparing substituted propargyl alcohol from phenylacetylene compounds and paraformaldehyde is as follows: Ref J + CHO), See R + La The number of r substituents can be 0-5.
2. The preparation method according to claim 1, which is characterized in that the type of R substituent can be selected from one or more of F, Br, CI, |, CN, CO;Et, CO,Me, Ac, ArCO, CFs, NO,, C1-8 alkyl, C1-8 alkoxy, Et, n-Pr, i-Pr, Bu, CH,=CH, OMe, OEt, OPr.
3. The preparation method according to claim 1, which is characterized in that the basic catalyst in step 2) can be selected from one of KOH, NaOH, K,COs;, TBA-OH, Cs:CO3, tetrabutyl ammonium hydroxide (TBA-OH), tetraethyl ammonium hydroxide (TEA-OH), tetramethyl ammonium hydroxide (TMA-OH).
4. The preparation method according to claim 3, which is characterized in that tetrabutylammonium hydroxide (TBA-OH) can be preferred as the base catalyst in step 2).
5. The preparation method according to claim 1, which is characterized in that the stirring rate of step 2) is 200-500r/min.
6.The preparation method according to claim 1, which is characterized in that the stirring rate of step 2) is 300r/min. 17905773 7The preparation method according to claim 1, which is characterized in that the heating temperature in step 3) is 40-60 C.
8.The preparation method according to claim 4, which is characterized in that the heating temperature in step 3) can be 40 C or 60 °C.
9.The preparation method according to claim 1, which is characterized in that the R substituent can be selected from one or more of F, Br, Cl. I. CN, CO;Et. CO,Me. Ac, ArCO, CFs NO.
10.The preparation method according to claim 1, which is characterized in that the R substituent can be selected from one or more of Me, Et, n-Pr. i-Pr. Bu, CHz=CH, OMe. OEt. OPr.
LU505773A 2022-12-15 2023-12-13 A base catalyzed method for preparing substituted propargyl alcohol from paraformaldehyde and alkyne LU505773B1 (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5110966A (en) * 1991-06-20 1992-05-05 Merrell Dow Pharmaceuticals Inc. New organoboron reagents for the preparation unsubstituted propargylic alcohols
US6710213B2 (en) * 2000-03-31 2004-03-23 Showa Denko K.K. Production process and use for propargyl alcohol and its intermediate
JP2002275109A (en) * 2001-03-21 2002-09-25 Maruzen Petrochem Co Ltd Method for separating and recovering propargyl alcohol
DE102004009311A1 (en) * 2004-02-26 2005-09-08 Basf Ag Process for the preparation of a propargyl alcohol and an allyl alcohol
CN108358749B (en) * 2018-02-07 2021-06-22 重庆弛源化工有限公司 Method for producing propargyl alcohol

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