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Production method of 7-dehydrocholesterol

A technology for the production of dehydrocholesterol, which is applied in the fields of steroids and organic chemistry, can solve problems such as unsuitable operation, complex production process, and large equipment investment, and achieve improved yield and purity, simple production process, and low equipment investment. small effect

Inactive Publication Date: 2017-03-15
SICHUAN YUXIN PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The existing processes all use bromine, with many side reactions and poor quality
Moreover, many steps need to be added to remove brominated by-products. Therefore, the actual production steps of the original process are various, resulting in a very complicated production process, which is not suitable for operation, large investment in equipment, and low efficiency.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] A kind of production method of 7-dehydrocholesterol, carries out following steps successively:

[0026] S1 First prepare benzoyl chloride, add 50kg of benzoic acid into the reaction kettle, heat and melt, pass through phosgene at 140°C for reaction, the temperature at the end of the reaction is -3°C, and then distill under reduced pressure to obtain benzoyl chloride.

[0027] In 150 mL of pyridine, 20 g of cholesterol was added, and 10 g of benzoyl chloride was added dropwise at a temperature of 50° C. (dropped in about 30 minutes). After the addition, the reaction was continued for 40 minutes to obtain 19.1 g of cholesterol benzoate.

[0028] S2 Add cholesterol benzoate and 50ml of carbon tetrachloride into a three-necked flask, protect it with nitrogen, stir and raise the temperature to 65°C, add 2.6g of 1,3-dibromo-5,5-dimethylhydantoin in portions , add 0.2g azobisisobutyronitrile as initiator, react for 5 hours, separate and purify after cooling to obtain 7-bromoch...

Embodiment 2

[0032] A kind of production method of 7-dehydrocholesterol, carries out following steps successively:

[0033] S1 First prepare benzoyl chloride, add 40kg of benzoic acid into the reaction kettle, heat and melt, pass through phosgene at 140°C for reaction, the temperature at the end of the reaction is -2°C, and then distill under reduced pressure to obtain benzoyl chloride.

[0034] In 130 mL of pyridine, 15 g of cholesterol was added, and 10 g of benzoyl chloride was added dropwise at a temperature of 55° C. (dropped in about 30 minutes). After the dropwise addition, the reaction was continued for 40 minutes to obtain 20.3 g of cholesterol benzoate.

[0035] S2 Add cholesterol benzoate and 45ml of carbon tetrachloride into a three-necked flask, protect it with nitrogen, stir and raise the temperature to 70°C, add 3.6g of 1,3-dibromo-5,5-dimethylhydantoin in portions , add 0.25g azobisisobutyronitrile as initiator, react for 4 hours, separate and purify after cooling to obtain...

Embodiment 3

[0039] A kind of production method of 7-dehydrocholesterol, carries out following steps successively:

[0040] S1 First prepare benzoyl chloride, add 30kg of benzoic acid into the reaction kettle, heat and melt, pass phosgene at 145°C for reaction, the temperature at the end of the reaction is -2°C, and then distill under reduced pressure to obtain benzoyl chloride.

[0041] In 120 mL of pyridine, 15 g of cholesterol was added, and 9 g of benzoyl chloride was added dropwise at a temperature of 55° C. (dropped in about 30 minutes). After the dropwise addition, the reaction was continued for 60 minutes to obtain 21.5 g of cholesterol benzoate.

[0042] S2 Add cholesterol benzoate and 45ml of carbon tetrachloride into a three-necked flask, protect it with nitrogen, stir and raise the temperature to 60°C, add 5.6g of 1,3-dibromo-5,5-dimethylhydantoin in portions , add 0.3g azobisisobutyronitrile as initiator, react for 4 hours, separate and purify after cooling to obtain 7-bromoch...

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PUM

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Abstract

The invention discloses a production method of 7-dehydrocholesterol. The method includes the steps: S1 dissolving cholesterol and benzoyl chloride in a solvent, and performing acylation reaction to obtain cholesteryl benzoate; S2 dissolving the cholesteryl benzoate and 1, 3-dibromo-5, 5-dimethyl hydantoin in the solvent, adding initiating agents, performing hydrazone reaction to obtain 7-bromo cholesterol benzoate; S3 dissolving the 7-bromo cholesterol benzoate and pyridine in ethyl alcohol, and performing hydrazone removal reaction to obtain 7-dehydrocholesterol benzoate; S4 adding the 7-dehydrocholesterol benzoate into sodium hydroxide solution, and performing saponification hydrolysis reaction to obtain the 7-dehydrocholesterol. The production method for the 7-dehydrocholesterol has the advantages of reasonable process, mild reaction condition, high selectivity, simplicity in operation, friendly environment and low production cost.

Description

technical field [0001] The invention relates to the field of fine chemical industry, in particular to a production method of 7-dehydrocholesterol. Background technique [0002] Vitamin D 3 (Vitamin D 3 ), also known as cholecalciferol, is a colorless crystal with a melting point of 84-85°C. It is a fat-soluble substance, insoluble in water, but soluble in solvents such as alcohol, ether, acetone, chloroform, and vegetable oil. Vitamin D 3 It is easy to oxidize and deactivate in humid air, but it can withstand high temperature and oxidation in neutral and alkaline solutions. Therefore, it should be stored in nitrogen, light-free and acid-free cold environment. [0003] Vitamins are found in human and most animal tissues. Human skin contains its precursor dehydrocholesterol, which can be transformed into vitamins under sunlight or ultraviolet radiation. Foods such as cod liver oil, liver, roe, butter, milk, and egg yolk are also rich in vitamins. Vitamin D 3 It is an es...

Claims

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Application Information

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IPC IPC(8): C07J9/00
CPCC07J9/00
Inventor 冷莉
Owner SICHUAN YUXIN PHARM CO LTD
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