GB518266A - A process for the manufacture of progesterone - Google Patents

A process for the manufacture of progesterone

Info

Publication number
GB518266A
GB518266A GB2170538A GB2170538A GB518266A GB 518266 A GB518266 A GB 518266A GB 2170538 A GB2170538 A GB 2170538A GB 2170538 A GB2170538 A GB 2170538A GB 518266 A GB518266 A GB 518266A
Authority
GB
United Kingdom
Prior art keywords
cholestenone
benzene
solution
acid
water
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB2170538A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Chinoin Private Co Ltd
Original Assignee
Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt filed Critical Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt
Priority to GB2170538A priority Critical patent/GB518266A/en
Publication of GB518266A publication Critical patent/GB518266A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

518,266. Progesterone. CHINOIN GYOGYSZER ES VEGYESZETI TERMEKEK GYARA R. T. (DR. KERESZTY & DR. WOLF) and BRETSCHNEIDER, H. July 21, 1938, No. 21705. [Class 2 (iii)] Progesterone is prepared by the oxidation of cholestenone characterized in that the oxidation takes place in the presence of sulphuric acid of a concentration greater than 50 per cent. The preferred oxidizing agents are chromic acid, chromic anhydride and chromates, and the preferred oxidation temperature between -5‹C. and +5‹C. The reaction mixture is worked up by dilution with much water followed by extraction with water immiscible solvents. A purification by means of a chromotographic separation may also be employed together with the use of ketone reagents. In examples : (1) A glacial acetic acid solution of cholestenone is introduced into an excess of strong sulphuric acid, and a solution of chromic anhydride in strong sulphuric acid is added. The oxidation takes place at -5‹C. for 4-5 hours, and the product is poured on to ice. The aqueous solution is extracted with benzene, and the benzene solution washed with caustic soda and water and evaporated. The residue is dissolved in acetone and crystallized to remove unchanged cholestenone. The acetone is evaporated, replaced by a benzene-benzine mixture, and washed with hydrochloric acid. The progesterone is extracted from the acid solution with ether and purified by a chromatographic separation. Instead of using glacial acetic acid as the solvent for the cholestenone, carbon tetrachloride may be sub- .stituted. (2) An acetic acid solution of cholestenone is added to concentrated sulphuric acid at 5‹C., and a sulphuric acid solution of chromic acid is then introduced. The oxidation mixture is poured on to ice extracted with benzene and washed with caustic soda and water. The residue after evaporation of the benzene is treated with petroleum ether and methyl alcohol and water to form two layers. After removal of unchanged cholestenone by extraction with methyl alcohol of the petroleum layer, there follows a series of extractions with benzene and methyl alcohol, finally followed by a chromatographic separation.
GB2170538A 1938-07-21 1938-07-21 A process for the manufacture of progesterone Expired GB518266A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2170538A GB518266A (en) 1938-07-21 1938-07-21 A process for the manufacture of progesterone

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2170538A GB518266A (en) 1938-07-21 1938-07-21 A process for the manufacture of progesterone

Publications (1)

Publication Number Publication Date
GB518266A true GB518266A (en) 1940-02-22

Family

ID=10167435

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2170538A Expired GB518266A (en) 1938-07-21 1938-07-21 A process for the manufacture of progesterone

Country Status (1)

Country Link
GB (1) GB518266A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115177965A (en) * 2022-07-11 2022-10-14 西安国康瑞金制药有限公司 System and method for recovering progesterone from progesterone production mother liquor

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115177965A (en) * 2022-07-11 2022-10-14 西安国康瑞金制药有限公司 System and method for recovering progesterone from progesterone production mother liquor
CN115177965B (en) * 2022-07-11 2023-04-25 西安国康瑞金制药有限公司 System and method for recovering progesterone from progesterone production mother liquor

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