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Synthesis method of ethyl 8-bromocaprylate

A technology of ethyl bromooctanoate and a synthetic method, which is applied in the field of synthesis of ethyl bromooctanoate, can solve the problems of many side reactions, low yield, and unsuitability for industrial production, and achieve few side reactions, simple process, easy to get effect

Pending Publication Date: 2021-07-09
SUZHOU HIGHFINE BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] However, in the first step in the above-mentioned report, the raw material 1,6-dichlorohexane reacts with diethyl malonate to synthesize 2-(6-chlorohexyl) diethyl malonate, and the process is prone to produce many substitution impurities leading to Yield is on the low side, and second step 2-(6-chlorohexyl) diethyl malonate and sulfuric acid high-temperature decarboxylation process have many side reactions so that this route is not suitable for suitability for industrialized production

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  • Synthesis method of ethyl 8-bromocaprylate
  • Synthesis method of ethyl 8-bromocaprylate
  • Synthesis method of ethyl 8-bromocaprylate

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preparation example Construction

[0029] According to the synthetic method of the 8-bromooctanoic acid ethyl ester of the embodiment of the present invention, comprise the steps:

[0030] Step S1, performing a substitution reaction between 1,6-dibromohexane and diethyl malonate to obtain the compound 2-(6-bromohexyl)-diethyl malonate.

[0031] That is, first, 1,6-dibromohexane and diethyl malonate are used for a substitution reaction to obtain 2-(6-bromohexyl)-diethyl malonate as an intermediate.

[0032] Its reaction formula is shown in following formula (3):

[0033]

[0034] Further, in the step S1, the substitution reaction is carried out in the first solvent under the action of the first base, wherein the first base is selected from sodium ethoxide, sodium methoxide, potassium carbonate, potassium tert-butoxide Any one of them, the first solvent is any one selected from acetonitrile, toluene, xylene, and carbon disulfide.

[0035] That is to say, the substitution reaction of the first step can be car...

Embodiment 1

[0061] S1: Pour diethyl malonate (100g 1.0eq), 1,6-dibromohexane (458kg 3.0eq), sodium ethoxide (46.7g 1.1eq) and solvent ethanol (500mL) into the reaction bottle and start stirring , temperature control reaction 30 ~ 40 degrees Celsius for 8 hours.

[0062] After the GC control reaction is complete, the solvent is removed under reduced pressure, the reaction is poured into ice water (200mL), and the organic layer is extracted with dichloromethane (200mL). After drying, the raw material is recovered by vacuum distillation, and then purified by distillation to obtain compound 2 -(6-bromohexyl)diethyl malonate 155g, yield 50%.

[0063] 1 H NMR (400MHz, CDCl 3 ) δ 3.77 (s, 4H), 3.40 (m, J = 10.9, 4.1 Hz, 3H), 2.00-1.77 (m, 6H), 1.57-1.04 (m, 10H).

[0064] S2: The compound 2-(6-bromohexyl)diethyl malonate (155g 1.0eq) was hydrolyzed with sodium hydroxide (38.4g2.0eq) for 2 hours under temperature control, and the reaction temperature was controlled at 25-40 degrees Celsius.

...

Embodiment 2

[0071] S1: The raw materials diethyl malonate (320g, 1.0eq), 1,6-dibromohexane (1.46kg, 3.0eq) and potassium carbonate (303g, 1.1eq) were poured into the reaction bottle and started to stir, and the temperature was controlled The reaction temperature is 65-75 degrees Celsius and the reaction is carried out for 10 hours.

[0072] The GC control reaction is complete, the reaction solution is poured into water to separate the organic layer, and the organic layer is dried and then subjected to vacuum distillation to first recover the raw materials, and then to obtain the compound 2-(6-bromohexyl)diethyl malonate 510g, yield 79%.

[0073] S2: The above-prepared compound 2-(6-bromohexyl)diethyl malonate (510g, 1.0eq) and potassium hydroxide (177g, 2.0eq) were subjected to a temperature-controlled hydrolysis reaction for 2h, and the reaction temperature was controlled for 25- 40 Celsius.

[0074] After the central control detects that there is no raw material, adjust the pH to acid...

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Abstract

The invention provides a synthesis method of ethyl 8-bromocaprylate, which comprises the following steps: S1, carrying out substitution reaction on 1,6-dibromohexane and diethyl malonate to obtain a compound 2-(6-bromohexyl)-diethyl malonate; S2, enabling the 2-(6-bromohexyl)-diethyl malonate to carry out ester hydrolysis and a decarboxylation reaction so as to obtain 8-bromocaprylic acid; and S3, carrying out an esterification reaction on the 8-bromocaprylic acid and absolute ethyl alcohol to obtain ethyl 8-bromocaprylate. According to the synthesis method of ethyl 8-bromocaprylate, disclosed by the embodiment of the invention, firstly, 1,6-dibromohexane initial raw material and diethyl malonate are subjected to substitution reaction to generate 2-(6-bromohexyl) diethyl malonate, and then ester hydrolysis and decarboxylation reaction are carried out to obtain 8-bromocaprylic acid; and finally,esterification reaction is carried out to generate ethyl 8-bromocaprylate. The raw materials are easy to obtain, side reactions in the reaction are few, the process is simple, and the method is suitable for industrial production, and has a very wide application prospect.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing ethyl 8-bromooctanoate. Background technique [0002] 8-Ethyl bromooctanoate is an excellent solvent and an important pharmaceutical and pesticide intermediate. The CAS number of ethyl 8-bromooctanoate is 105484-55-7, and structural formula is as shown in following formula (1): [0003] [0004] Currently, there is little literature on the synthesis of ethyl 8-bromooctanoate. Reference. It is known that there is a report on the synthesis of ethyl 8-chlorooctanoate, which uses 1,6-dichlorohexane and diethyl malonate as initial raw materials, supplemented by phase transfer catalysts such as tetramethylammonium bromide (TMAC), Powder potassium carbonate is done alkali synthesis 2-(6-chlorohexyl) diethyl malonate, then selective reaction under sulfuric acid condition obtains 8-chlorooctanoic acid ethyl ester, and its synthetic route is as sho...

Claims

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Application Information

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IPC IPC(8): C07C67/343C07C69/38C07C27/02C07C51/09C07C51/38C07C53/19C07C67/08C07C69/63
CPCC07C67/343C07C51/09C07C51/38C07C67/08C07C69/38C07C53/19C07C69/63
Inventor 顾寿胜吕敏杰
Owner SUZHOU HIGHFINE BIOTECH