CN110818560A - Preparation method of 4-benzyloxy phenyl ethyl n-decanoate - Google Patents
Preparation method of 4-benzyloxy phenyl ethyl n-decanoate Download PDFInfo
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- CN110818560A CN110818560A CN201911211624.7A CN201911211624A CN110818560A CN 110818560 A CN110818560 A CN 110818560A CN 201911211624 A CN201911211624 A CN 201911211624A CN 110818560 A CN110818560 A CN 110818560A
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- decanoate
- benzyloxy
- benzyloxy phenyl
- phenyl ethyl
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of 4-benzyloxy phenyl ethyl n-decanoate, which comprises the step of carrying out esterification reaction on 4-benzyloxy phenyl ethanol and n-decanoic acid under the conditions of p-toluenesulfonic acid catalysis and desiccant dehydration to obtain the 4-benzyloxy phenyl ethyl n-decanoate. The invention overcomes the side reaction of intramolecular dehydration caused by overhigh temperature, and adopts the 4-benzyloxy phenethyl alcohol and the n-decanoic acid to carry out esterification reaction under the conditions of p-toluenesulfonic acid catalysis and desiccant dehydration to obtain the 4-benzyloxy phenethyl n-decanoate.
Description
Technical Field
The invention belongs to the field of chemistry, and particularly relates to a green quantitative synthesis method of a thermochromic additive 4-benzyloxy phenyl ethyl n-decanoate.
Background
4-benzyloxy phenyl ethyl n-decanoate is a thermochromic assistant and can be used in erasable pen ink. It is usually obtained by reacting 4-benzyloxyphenethyl alcohol with n-decanoyl chloride, but the reaction is slow and is easily inactivated to some extent, and therefore, an improvement is required. The direct esterification of 4-benzyloxy phenethyl alcohol and n-decanoic acid under acid catalysis is rarely reported, but 4-benzyloxy phenethyl alcohol is easy to dehydrate under the condition of higher temperature under acid catalysis, side reaction occurs, the yield is reduced, and the product is impure.
Disclosure of Invention
In order to solve the technical problem, the invention discloses a preparation method of 4-benzyloxy phenyl ethyl n-decanoate. The invention overcomes the side reaction of intramolecular dehydration caused by overhigh temperature, and adopts the 4-benzyloxy phenethyl alcohol and the n-decanoic acid to carry out esterification reaction under the conditions of p-toluenesulfonic acid catalysis and desiccant dehydration to obtain the 4-benzyloxy phenethyl n-decanoate.
The purpose of the invention is realized by the following technical scheme:
a preparation method of 4-benzyloxy phenyl ethyl n-decanoate adopts 4-benzyloxy phenyl ethanol and n-decanoic acid to carry out esterification reaction under the conditions of p-toluenesulfonic acid catalysis and desiccant dehydration to obtain 4-benzyloxy phenyl ethyl n-decanoate, and the general formula is as follows:
the further improvement is characterized in that the dosage of the p-toluenesulfonic acid is 5-10% of the mass of the 4-benzyloxy phenethyl alcohol.
In a further improvement, the drying agent is any mixture of anhydrous magnesium sulfate, anhydrous sodium sulfate or anhydrous calcium chloride, and the used mass is 10-80% of the mass of the 4-benzyloxy phenethyl alcohol.
Further improvement, the temperature of the esterification reaction of the 4-benzyloxy phenethyl alcohol and the n-decanoic acid is 30-70 ℃.
The further improvement is that the mass ratio of the 4-benzyloxy phenethyl alcohol to the n-decanoic acid is 11.4: 9.5-9.6.
Detailed Description
The present invention will be described in further detail with reference to examples, but the embodiments of the present invention are not limited thereto.
The synthetic chemical formula of the 4-benzyloxy phenethyl decanoate prepared by the invention is as follows:
the present invention will be described in further detail with reference to examples.
Example 1
22.8g of 4-benzyloxy phenethyl alcohol, 220g of toluene, 3g of p-toluenesulfonic acid, 19.2g of n-decanoic acid and 8.0g of anhydrous magnesium sulfate are added into a 500 ml reaction kettle, the temperature is raised to 40-70 ℃, the reaction is started, the reaction time is 12 hours, the reaction is stopped, 100g of saturated sodium carbonate solution is used for washing once, liquid separation is carried out, anhydrous magnesium sulfate is used for drying, desolventization is carried out, a crude product is obtained, and 40g of n-hexane is used for recrystallization.
Example 2
In a 500 ml reaction kettle, 11.4g 4-benzyloxy phenethyl alcohol, 120g toluene, 1.5g p-toluenesulfonic acid, 9.5g n-capric acid and 6.0g anhydrous sodium sulfate are added, the temperature is raised to 40-70 ℃, the reaction is started, the reaction time is 12 hours, the reaction is stopped, 100g saturated sodium carbonate solution is used for washing, liquid separation, anhydrous magnesium sulfate drying and desolventizing are carried out, a crude product is obtained, and 20g n-hexane is used for recrystallization.
Example 3
In a 500 ml reaction kettle, 11.4g 4-benzyloxy phenethyl alcohol, 120g toluene, 1.5g p-toluenesulfonic acid, 9.5g n-capric acid and 7.0g anhydrous calcium chloride are added, the temperature is raised to 40-70 ℃, the reaction is started, the reaction time is 12 hours, the reaction is stopped, 100g saturated sodium carbonate solution is used for washing, liquid separation, anhydrous magnesium sulfate drying and desolventizing are carried out, a crude product is obtained, and 20g n-hexane is used for recrystallization.
While embodiments of the invention have been described above, it is not limited to the applications set forth in the specification and the embodiments, which are fully applicable to various fields of endeavor for which the invention pertains, and further modifications may readily be made by those skilled in the art, it being understood that the invention is not limited to the specific details shown and described herein without departing from the general concept defined by the claims and their equivalents.
Claims (5)
1. A preparation method of 4-benzyloxy phenyl ethyl n-decanoate is characterized in that 4-benzyloxy phenyl ethanol and n-decanoic acid are adopted to carry out esterification reaction under the conditions of p-toluenesulfonic acid catalysis and desiccant dehydration to obtain the 4-benzyloxy phenyl ethyl n-decanoate, and the general formula is as follows:
2. the process for producing 4-benzyloxyphenylethyl n-decanoate according to claim 1, wherein the p-toluenesulfonic acid is used in an amount of 5 to 10% by mass based on the mass of 4-benzyloxyphenethyl alcohol.
3. The method for producing 4-benzyloxyphenylethyl n-decanoate according to claim 1, wherein the drying agent is a mixture of anhydrous magnesium sulfate, anhydrous sodium sulfate or anhydrous calcium chloride, and the mass used is 40 to 50% of the mass of 4-benzyloxyphenethyl alcohol.
4. The process for producing 4-benzyloxyphenylethyl n-decanoate according to claim 1, wherein the esterification reaction temperature of 4-benzyloxyphenylethanol with n-decanoic acid is 30 to 70 ℃.
5. The process for producing 4-benzyloxyphenylethyl n-decanoate according to claim 1, wherein the mass ratio of 4-benzyloxyphenylethanol to n-decanoic acid is 11.4: 9.5-9.6.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911211624.7A CN110818560A (en) | 2019-12-02 | 2019-12-02 | Preparation method of 4-benzyloxy phenyl ethyl n-decanoate |
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| CN201911211624.7A CN110818560A (en) | 2019-12-02 | 2019-12-02 | Preparation method of 4-benzyloxy phenyl ethyl n-decanoate |
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| CN110818560A true CN110818560A (en) | 2020-02-21 |
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| CN201911211624.7A Pending CN110818560A (en) | 2019-12-02 | 2019-12-02 | Preparation method of 4-benzyloxy phenyl ethyl n-decanoate |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114213248A (en) * | 2021-12-08 | 2022-03-22 | 郑州睿嘉纳米新材料科技有限公司 | Preparation method of 4-benzyloxy phenyl ethyl n-decanoate |
| WO2022236524A1 (en) * | 2021-05-10 | 2022-11-17 | 怀化金鑫新材料有限公司 | Photoinitiator and preparation method therefor |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62181236A (en) * | 1986-02-04 | 1987-08-08 | Nisshin Oil Mills Ltd:The | Novel ester and cosmetic containing said ester |
| CN102030638A (en) * | 2010-11-18 | 2011-04-27 | 浙江皇马科技股份有限公司 | Preparation process of neopentyl polyacohol octocapric acid ester |
| CN102229529A (en) * | 2011-05-11 | 2011-11-02 | 华诺森（武汉）生物医药技术有限公司 | Preparation method of (methyl) crylic acid phenylethanol ester compounds |
| CN103965041A (en) * | 2013-02-06 | 2014-08-06 | 华烁科技股份有限公司 | Method for preparing 2-(4-benzyloxy phenyl)ethanol fatty acid ester |
| CN110015957A (en) * | 2019-03-30 | 2019-07-16 | 镇江巨杰新材料技术研发中心(有限合伙) | A kind of synthetic method and application of polyethylene glycol 400 tricaprylate |
-
2019
- 2019-12-02 CN CN201911211624.7A patent/CN110818560A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62181236A (en) * | 1986-02-04 | 1987-08-08 | Nisshin Oil Mills Ltd:The | Novel ester and cosmetic containing said ester |
| CN102030638A (en) * | 2010-11-18 | 2011-04-27 | 浙江皇马科技股份有限公司 | Preparation process of neopentyl polyacohol octocapric acid ester |
| CN102229529A (en) * | 2011-05-11 | 2011-11-02 | 华诺森（武汉）生物医药技术有限公司 | Preparation method of (methyl) crylic acid phenylethanol ester compounds |
| CN103965041A (en) * | 2013-02-06 | 2014-08-06 | 华烁科技股份有限公司 | Method for preparing 2-(4-benzyloxy phenyl)ethanol fatty acid ester |
| CN110015957A (en) * | 2019-03-30 | 2019-07-16 | 镇江巨杰新材料技术研发中心(有限合伙) | A kind of synthetic method and application of polyethylene glycol 400 tricaprylate |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022236524A1 (en) * | 2021-05-10 | 2022-11-17 | 怀化金鑫新材料有限公司 | Photoinitiator and preparation method therefor |
| CN114213248A (en) * | 2021-12-08 | 2022-03-22 | 郑州睿嘉纳米新材料科技有限公司 | Preparation method of 4-benzyloxy phenyl ethyl n-decanoate |
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