CN110452102A - A kind of synthetic method of 3- methoxyl group -3- methyl butyne - Google Patents
A kind of synthetic method of 3- methoxyl group -3- methyl butyne Download PDFInfo
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- CN110452102A CN110452102A CN201910815088.5A CN201910815088A CN110452102A CN 110452102 A CN110452102 A CN 110452102A CN 201910815088 A CN201910815088 A CN 201910815088A CN 110452102 A CN110452102 A CN 110452102A
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- methoxyl group
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- 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
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
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Abstract
The invention discloses a kind of synthetic method of 3- methoxyl group -3- methyl butyne, this method first synthesizes -3 alcohol of 3- methyl butyne using acetone and acetylene as starting material, then reacts with dimethyl suflfate, obtains 3- methoxyl group -3- methyl butyne.The synthetic method of 3- methoxyl group -3- methyl butyne provided by the invention, cost of material used in the synthetic method is low, it is low in cost, be easy to get, and synthetic route of the present invention is short, yield is high, obtained product chemistry purity is high, all reactions are not required to special producing equipment, and gained intermediate and final product are all not required to column chromatography and crystallization purifying.
Description
Technical field
The invention belongs to medicine, chemical technology field, and in particular to a kind of synthesis side of 3- methoxyl group -3- methyl butyne
Method.
Background technique
3- methoxyl group -3- methyl butyne is a kind of important organic synthesis intermediate, can be widely used for medicine, pesticide
With the preparation of a variety of materials.For the document report of synthesis 3- methoxyl group -3- methyl butyne, the existing similar patent in the country, including
The number of applying for a patent 108863717；The number of applying for a patent 106831332；The number of applying for a patent 106117010.Also there are the similar phase in foreign countries
Periodical report, such as: Journal of Organic Chemistry, 21,4663-4670,2014；Journal of Applied
Polymer Science, 120 (6), 3363-3369,2011；Russian Chemical Bulletin, 57(10),
2111-2116,2008.But the reaction condition of above-mentioned synthetic method is harsher, yield is lower, is not easy to amplify production.
Summary of the invention
The technical problem to be solved by the present invention is to overcome the defects of the prior art, provide a kind of 3- methoxyl group -3- methyl fourth
The synthetic method of alkynes.
In order to solve the above technical problems, the technical solution adopted by the present invention is that:
A kind of synthetic method of 3- methoxyl group -3- methyl butyne, comprising the following steps:
A1: reacting acetone with the acetylene dimethyl sulphoxide solution of saturation, -3 alcohol of I: 3- methyl butyne of production；
A 2: -3 alcohol of 3- methyl butyne is reacted with dimethyl suflfate, obtains II: 3- methoxyl group -3- methyl butyne of formula；
。
Preferably, in step a1, by acetylene gas be passed into potassium hydroxide dimethyl sulfoxide mix solution in until
Acetone is added dropwise under conditions of 10-15 DEG C in saturation；
The molar ratio of the potassium hydroxide and acetone is 0.05~1:0.06~1；
Reacting the organic solvent used is dimethyl sulfoxide, the volume ratio of acetone and dimethyl sulfoxide are as follows: 40~1:50~1；
The reaction time of logical acetylene is 7~9h；
Reaction solution after having reacted is neutralized through carbon dioxide, filtering, is concentrated under reduced pressure, distillation, obtains -3 alcohol of I: 3- methyl butyne of formula.
Preferably, in step a2, formula I and dimethyl suflfate (1.1 ~ 1.3 equivalent) are added drop-wise to hydroxide at 15-20 DEG C
It reacts in the solution of potassium hydrate and dimethylformamide, is reacted at 15-20 DEG C, extracted, be concentrated, distillation obtains formula II:
The molar ratio of 3- methoxyl group -3- methyl butyne, formula I and dimethyl suflfate is 1:1.1~1.3.
Preferably, the volume ratio of -3 alcohol of 3- methyl butyne and dimethylformamide is 1:4~5.
Preferably, the reaction time of -3 alcohol of 3- methyl butyne and dimethyl suflfate is 0.5~1h.
Advantageous effects of the invention:
The present invention provides a kind of synthetic method of 3- methoxyl group -3- methyl butyne, used cost of material is low, at low cost
It is honest and clean, be easy to get, and synthetic route of the present invention is short, yield is high, and obtained product chemistry purity is high, it is special that all reactions are not required to
Production equipment, gained intermediate and final product are all not required to column chromatography and crystallization purifying, reduce production cost, put convenient for industry
Mass production provides high purity product for market, has high economic benefit.
Detailed description of the invention
Fig. 1 is synthetic route chart of the invention；
Fig. 2 is the GC spectrogram of 3- methoxyl group -3- methyl butyne of the invention；
Fig. 3 is the nuclear magnetic spectrogram of 3- methoxyl group -3- methyl butyne of the invention.
Specific embodiment
The invention will be further described below in conjunction with the accompanying drawings.Following embodiment is only used for clearly illustrating the present invention
Technical solution, and not intended to limit the protection scope of the present invention.
Embodiment 1
As shown in Figure 1-3, the synthetic method of -3 alcohol of 3- methyl butyne, includes the following steps:
By in 9.8 grams of raw material potassium hydroxide hydrate (0.15 mol) addition 500ml dimethyl sulfoxides, at 10-15 DEG C, it is passed through
Acetylene gas is saturated after about 7 hours.At this temperature, 160 grams of acetone (2.76 mol) is added dropwise, 7h is added dropwise；Continuing to lead to
In the case where entering acetylene, react 2 hours.It is passed through carbon dioxide gas neutralization reaction system, filters out solid, filtrate decompression concentration
Distillation collects 50-150 ° of fraction and obtains 190 grams of -3 alcohol of 3- methyl butyne, purity 98%, yield 82%, the retention time of product
For 6.32min.
1H NMR(CDCl3):δ= 1.44 (s,6H,CH3, CH3),δ= 2.41(s,1H,-C CH),δ= 3.35(s,
3H,-OCH3) ppm。
Embodiment 2
As shown in Figure 1, the synthetic method of -3 alcohol of 3- methyl butyne, includes the following steps:
By in 9.8 grams of raw material potassium hydroxide hydrate (0.15 mol) addition 500ml dimethyl sulfoxides, under 20-25 DEG C of degree, lead to
It is saturated after entering acetylene gas about 7 hours.At this temperature, 160 grams of acetone (2.76 mol) is added dropwise to be added dropwise for about 7 hours.In
Continue in the case where being passed through acetylene, reacts 2 hours.It is passed through carbon dioxide gas neutralization reaction system, filters out solid, filtrate subtracts
Pressure concentration distillation, the fraction for collecting 50-150 degree obtain 120 grams of -3 alcohol of 3- methyl butyne, purity 95%, yield: 52%.
Remaining same embodiment 1.
Embodiment 3
As shown in Figure 1, the synthetic method of -3 alcohol of 3- methyl butyne, includes the following steps:
By in 9.8 grams of raw material potassium hydroxide hydrate (0.15 mol) addition 400ml dimethyl sulfoxides, under 10-15 DEG C of degree, lead to
It is saturated after entering acetylene gas about 7 hours.At this temperature, 160 grams of acetone (2.76 mol) is added dropwise to be added dropwise for about 7 hours.In
Continue in the case where being passed through acetylene, reacts 2 hours.It is passed through carbon dioxide gas neutralization reaction system, filters out solid, filtrate subtracts
Pressure concentration distillation, the fraction for collecting 50-150 degree obtain 155 grams of -3 alcohol of 3- methyl butyne, purity 96%, yield: 67%.
Remaining same embodiment 1.
Embodiment 4
As shown in Figure 1, the synthetic method of -3 alcohol of 3- methyl butyne, includes the following steps:
By in 9.8 grams of raw material potassium hydroxide hydrate (0.15 mol) addition 450ml dimethyl sulfoxides, under 10-15 DEG C of degree, lead to
It is saturated after entering acetylene gas about 7 hours.At this temperature, 160 grams of acetone (2.76 mol) is added dropwise to be added dropwise for about 7 hours.In
Continue in the case where being passed through acetylene, reacts 2 hours.It is passed through carbon dioxide gas neutralization reaction system, filters out solid, filtrate subtracts
Pressure concentration distillation, the fraction for collecting 50-150 degree obtain 164 grams of -3 alcohol of 3- methyl butyne, purity 97%, yield: 74%.
Embodiment 5
As shown in Figure 1, the synthetic method of -3 alcohol of 3- methyl butyne, includes the following steps:
By in 10.8 grams of raw material potassium hydroxide hydrate (0.16 mol) addition 500ml dimethyl sulfoxides, under 10-15 DEG C of degree,
It is saturated after being passed through acetylene gas about 7 hours.At this temperature, 160 grams of acetone (2.76 mol) is added dropwise to be added dropwise for about 2 hours.
In the case where continuing to be passed through acetylene, then react 2 hours.It is passed through carbon dioxide gas neutralization reaction system, filters out solid, is filtered
Distillation is concentrated under reduced pressure in liquid, and the fraction for collecting 50-150 degree obtains 155 grams of -3 alcohol of 3- methyl butyne, purity 96%, yield: 67%.
Embodiment 6
As shown in Figure 1, the synthetic method of -3 alcohol of 3- methyl butyne, includes the following steps:
By in 10.3 grams of raw material potassium hydroxide hydrate (0.155 mol) addition 500ml dimethyl sulfoxides, under 10-15 DEG C of degree,
It is saturated after being passed through acetylene gas about 7 hours.At this temperature, 160 grams of acetone (2.76 mol) is added dropwise to be added dropwise for about 2 hours.
In the case where continuing to be passed through acetylene, react 2 hours.It is passed through carbon dioxide gas neutralization reaction system, filters out solid, filtrate
Distillation is concentrated under reduced pressure, the fraction for collecting 50-150 degree obtains 167 grams of -3 alcohol of 3- methyl butyne, purity 97%, yield: 72%.
Embodiment 7
As shown in Figure 1, the synthetic method of 3- methoxyl group -3- methyl butyne, includes the following steps:
Potassium hydroxide (67g, 1.1mol) is added in the n,N-Dimethylformamide solution of 420ml, is added dropwise under 15-20 degree
- 3 alcohol of 3- methyl butyne (84 g, 1.0 mol).15min is stirred at this temperature, is added dropwise dimethyl suflfate (139g, 1.1 mol)
It drips within about 2 hours, at this temperature insulation reaction 1 hour.GC tracing detection, will be anti-to -3 alcohol fully reacting of 3- methyl butyne
Liquid is answered to be poured into ice water, methyl tertiary butyl ether(MTBE) extracts 3 times, merges methyl tertiary butyl ether(MTBE) organic layer, salt water washing 2 times, anhydrous
Sodium sulphate is dry, filters, and filtrate decompression concentration distillation, the fraction for collecting 50-120 degree obtains 86 grams of 3- methoxyl group -3- methyl fourths
Alkynes, purity 98%, yield: 88%.
Embodiment 8
As shown in Figure 1, the synthetic method of 3- methoxyl group -3- methyl butyne, includes the following steps:
Potassium hydroxide (67g, 1.1mol) is added in the n,N-Dimethylformamide solution of 420ml, is added dropwise under 15-20 degree
- 3 alcohol of 3- methyl butyne (84 g, 1.0 mol).It stirs 15 minutes at this temperature, and dropwise addition dimethyl suflfate (151 g, 1.2
Mol it) drips within about 2 hours, at this temperature insulation reaction 1 hour.GC tracing detection to -3 alcohol fully reacting of 3- methyl butyne,
Reaction solution is poured into ice water, methyl tertiary butyl ether(MTBE) extracts 3 times, merging methyl tertiary butyl ether(MTBE) organic layer, and salt water washing 2 times,
Anhydrous sodium sulfate is dry, filters, and filtrate decompression concentration distillation, the fraction for collecting 50-120 degree obtains 90 grams of 3- methoxyl group -3- first
Base butine, purity 98%, yield: 92%.
Embodiment 9
As shown in Figure 1, the synthetic method of 3- methoxyl group -3- methyl butyne, includes the following steps:
Potassium hydroxide (67g, 1.1mol) is added in the n,N-Dimethylformamide solution of 420ml, is added dropwise under 15-20 degree
- 3 alcohol of 3- methyl butyne (84 g, 1.0 mol).It stirs 15 minutes at this temperature, and dropwise addition dimethyl suflfate (164 g, 1.3
Mol it) drips within about 2 hours, at this temperature insulation reaction 1 hour.GC tracing detection to -3 alcohol fully reacting of 3- methyl butyne,
Reaction solution is poured into ice water, methyl tertiary butyl ether(MTBE) extracts 3 times, merging methyl tertiary butyl ether(MTBE) organic layer, and salt water washing 2 times,
Anhydrous sodium sulfate is dry, filters, and filtrate decompression concentration distillation, the fraction for collecting 50-120 degree obtains 87 grams of 3- methoxyl group -3- first
Base butine, purity 96%, yield: 89%.
Embodiment 10
As shown in Figure 1, the synthetic method of 3- methoxyl group -3- methyl butyne, includes the following steps:
Potassium hydroxide (67 g, 1.1mol) is added in the n,N-Dimethylformamide solution of 330ml, is dripped under 15-20 degree
Add -3 alcohol of 3- methyl butyne (84 g, 1.0 mol).It stirs 15 minutes at this temperature, and dropwise addition dimethyl suflfate (139 g, 1.1
Mol it) drips within about 2 hours, at this temperature insulation reaction 1 hour.GC tracing detection to -3 alcohol fully reacting of 3- methyl butyne,
Reaction solution is poured into ice water, methyl tertiary butyl ether(MTBE) extracts 3 times, merging methyl tertiary butyl ether(MTBE) organic layer, and salt water washing 2 times,
Anhydrous sodium sulfate is dry, filters, and filtrate decompression concentration distillation, the fraction for collecting 50-120 degree obtains 76 grams of 3- methoxyl group -3- first
Base butine, purity 97%, yield: 78%.
Embodiment 11
As shown in Figure 1, the synthetic method of 3- methoxyl group -3- methyl butyne, includes the following steps:
Potassium hydroxide (67 g, 1.1mol) is added in the n,N-Dimethylformamide solution of 378ml, is dripped under 15-20 degree
Add -3 alcohol of 3- methyl butyne (84 g, 1.0 mol).It stirs 15 minutes at this temperature, and dropwise addition dimethyl suflfate (139 g, 1.1
Mol it) drips within about 2 hours, at this temperature insulation reaction 1 hour.GC tracing detection to -3 alcohol fully reacting of 3- methyl butyne,
Reaction solution is poured into ice water, methyl tertiary butyl ether(MTBE) extracts 3 times, merging methyl tertiary butyl ether(MTBE) organic layer, and salt water washing 2 times,
Anhydrous sodium sulfate is dry, filters, and filtrate decompression concentration distillation, the fraction for collecting 50-120 degree obtains 82 grams of 3- methoxyl group -3- first
Base butine, purity 97%, yield: 84%.
Embodiment 12
As shown in Figure 1, the synthetic method of 3- methoxyl group -3- methyl butyne, includes the following steps:
Potassium hydroxide (67 g, 1.1 mol) is added in the n,N-Dimethylformamide solution of 420ml, is dripped under 15-20 degree
Add -3 alcohol of 3- methyl butyne (84 g, 1.0 mol).It stirs 15 minutes at this temperature, and dropwise addition dimethyl suflfate (139 g, 1.1
Mol it) drips within about 2 hours, at this temperature insulation reaction half an hour.GC tracing detection to -3 alcohol of 3- methyl butyne has reacted
Entirely, reaction solution is poured into ice water, methyl tertiary butyl ether(MTBE) extracts 3 times, merges methyl tertiary butyl ether(MTBE) organic layer, salt water washing 2
Secondary, anhydrous sodium sulfate is dry, filters, and filtrate decompression concentration distillation, the fraction for collecting 50-120 degree obtains 83 grams of 3- methoxyl group -3-
Methyl butyne, purity 98%, yield: 85%.
Embodiment 13
As shown in Figure 1, the synthetic method of 3- methoxyl group -3- methyl butyne, includes the following steps:
Potassium hydroxide (67 g, 1.1 mol) is added in the n,N-Dimethylformamide solution of 420ml, is dripped under 25-30 degree
Add -3 alcohol of 3- methyl butyne (84 g, 1.0 mol).It stirs 15 minutes at this temperature, and dropwise addition dimethyl suflfate (139 g, 1.1
Mol it) drips within about 2 hours, at this temperature insulation reaction 1 hour.GC tracing detection to -3 alcohol fully reacting of 3- methyl butyne,
Reaction solution is poured into ice water, methyl tertiary butyl ether(MTBE) extracts 3 times, merging methyl tertiary butyl ether(MTBE) organic layer, and salt water washing 2 times,
Anhydrous sodium sulfate is dry, filters, and filtrate decompression concentration distillation, the fraction for collecting 50-120 degree obtains 63 grams of 3- methoxyl group -3- first
Base butine, purity 95%, yield: 65%.
The above is only a preferred embodiment of the present invention, it is noted that for the ordinary skill people of the art
For member, without departing from the technical principles of the invention, several improvement and deformations can also be made, these improvement and deformations
Also it should be regarded as protection scope of the present invention.
Claims (7)
1. a kind of synthetic method of 3- methoxyl group -3- methyl butyne, which comprises the following steps:
A1: make acetone and acetylene reaction, -3 alcohol of I: 3- methyl butyne of production；
A2: formula I is reacted with dimethyl suflfate, obtains II: 3- methoxyl group -3- methyl butyne of formula；
。
2. a kind of synthetic method of 3- methoxyl group -3- methyl butyne according to claim 1, which is characterized in that including with
Lower step:
A1: in the presence of potassium hydroxide is hydrated object and dimethyl sulfoxide, acetone and acetylene reaction maintain the temperature at 10~15 DEG C,
It is stirred to react 7~9h, neutralizes, filter through carbon dioxide, filtrate obtains formula I through distillation；
A2: formula I and dimethyl suflfate are added drop-wise to the solution of potassium hydroxide hydration object and dimethylformamide at 15~20 DEG C
Middle reaction is extracted, is concentrated, and distillation obtains formula II.
3. a kind of synthetic method of 3- methoxyl group -3- methyl butyne according to claim 2, which is characterized in that step a1
In, it is 0.05~1:0.06~1 that potassium hydroxide, which is hydrated object and the molar ratio of acetone,.
4. a kind of synthetic method of 3- methoxyl group -3- methyl butyne according to claim 2, which is characterized in that step a1
In, the volume ratio of acetone and dimethyl sulfoxide are as follows: 40~1:50~1.
5. a kind of synthetic method of 3- methoxyl group -3- methyl butyne according to claim 2, which is characterized in that step a2
In, the molar ratio of formula I and dimethyl suflfate is 1:1.1~1.3.
6. a kind of synthetic method of 3- methoxyl group -3- methyl butyne according to claim 2, which is characterized in that step a2
In, the volume ratio of formula I and dimethylformamide are as follows: 1:4~5.
7. a kind of synthetic method of 3- methoxyl group -3- methyl butyne according to claim 2, which is characterized in that step a2
In, the reaction time of formula I and dimethyl suflfate is 0.5~1h.
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| CN1554632A (en) * | 2003-12-26 | 2004-12-15 | 南京林业大学 | Synthetic method for propylend glycol dimethyl ether |
| CN101186562A (en) * | 2007-12-06 | 2008-05-28 | 大连理工大学 | Low energy-consumption high conversion and selectivity fast synthesis method for aryl methyl ether |
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2019
- 2019-08-30 CN CN201910815088.5A patent/CN110452102A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1554632A (en) * | 2003-12-26 | 2004-12-15 | 南京林业大学 | Synthetic method for propylend glycol dimethyl ether |
| CN101186562A (en) * | 2007-12-06 | 2008-05-28 | 大连理工大学 | Low energy-consumption high conversion and selectivity fast synthesis method for aryl methyl ether |
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| Title |
|---|
| B. A. TROFIMOV 等: "The Role of Potassium Cation inthe Favorskii Ethynylation of Acetone: Effekt of Dibenzo-18-crown-6", 《RUSSIAN JOURNAL OF ORGANIC CHEMISTRY》 * |
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