WO2023086447A3 - A method for the synthesis of cannabinol - Google Patents

A method for the synthesis of cannabinol Download PDF

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Publication number
WO2023086447A3
WO2023086447A3 PCT/US2022/049504 US2022049504W WO2023086447A3 WO 2023086447 A3 WO2023086447 A3 WO 2023086447A3 US 2022049504 W US2022049504 W US 2022049504W WO 2023086447 A3 WO2023086447 A3 WO 2023086447A3
Authority
WO
WIPO (PCT)
Prior art keywords
cannabinol
compound
synthesis
pentylbenzene
methylating
Prior art date
Application number
PCT/US2022/049504
Other languages
French (fr)
Other versions
WO2023086447A2 (en
Inventor
Narender POTTABATHINI
Srivinas KOLA
Marc BENCIVENGA
Surendra Singh
Original Assignee
Pureform Global, Inc.
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 Pureform Global, Inc. filed Critical Pureform Global, Inc.
Publication of WO2023086447A2 publication Critical patent/WO2023086447A2/en
Publication of WO2023086447A3 publication Critical patent/WO2023086447A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

Disclosed herein is a method for making cannabinol. Cannabinol. The method comprises coupling a protected 3,5-dihydroxy-1-pentylbenzene compound with a 4-methylbenzoate compound, cyclizing the coupled intermediate, and methylating the cyclized compound to form cannabinol.
PCT/US2022/049504 2021-11-12 2022-11-10 A method for the synthesis of cannabinol WO2023086447A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202163278619P 2021-11-12 2021-11-12
US63/278,619 2021-11-12

Publications (2)

Publication Number Publication Date
WO2023086447A2 WO2023086447A2 (en) 2023-05-19
WO2023086447A3 true WO2023086447A3 (en) 2023-07-06

Family

ID=86336731

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2022/049504 WO2023086447A2 (en) 2021-11-12 2022-11-10 A method for the synthesis of cannabinol

Country Status (1)

Country Link
WO (1) WO2023086447A2 (en)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20170008869A1 (en) * 2015-07-10 2017-01-12 Noramco, Inc. Process for the production of cannabidiol and delta-9-tetrahydrocannabinol
US20200199056A1 (en) * 2017-09-01 2020-06-25 Pureform Global, Inc. Synthetic cannabidiol compositions and methods of making the same
WO2022187935A1 (en) * 2021-03-11 2022-09-15 Kare Chemical Technologies Inc. Catalytic cannabinol synthesis and precursors

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20170008869A1 (en) * 2015-07-10 2017-01-12 Noramco, Inc. Process for the production of cannabidiol and delta-9-tetrahydrocannabinol
US20200199056A1 (en) * 2017-09-01 2020-06-25 Pureform Global, Inc. Synthetic cannabidiol compositions and methods of making the same
WO2022187935A1 (en) * 2021-03-11 2022-09-15 Kare Chemical Technologies Inc. Catalytic cannabinol synthesis and precursors

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
COMBS DONALD W.: "Synthesis of oxygenated derivatives of dibenzo-[b,d]pyran-6-one as precursors for lycorine- and crinine-type alkaloids; Part II", PHD DISSERTATION, IOWA STATE UNIVERSITY, 1 January 1978 (1978-01-01), XP093078707, Retrieved from the Internet <URL:https://core.ac.uk/download/pdf/38898429.pdf> [retrieved on 20230905] *
DATABASE PUBCHEM SUBSTANCE ANONYMOUS : "SID 163461169", XP093078710, retrieved from PUBCHEM *
NORSEEDA KRISSADA, TUMMATORN JUMREANG, KRAJANGSRI SUPPACHAI, THONGSORNKLEEB CHARNSAK, RUCHIRAWAT SOMSAK: "Synthesis of 6-Alkyl-6 H -benzo[ c ]chromene Derivatives by Cyclization/Selective Ether Cleavage in One Pot: Total Synthesis of Cannabinol", ASIAN JOURNAL OF ORGANIC CHEMISTRY , 1(2), 160-165 CODEN: AJOCC7; ISSN: 2193-5807, WILEY - V C H VERLAG GMBH & CO. KGAA, GERMANY, vol. 5, no. 6, 1 June 2016 (2016-06-01), Germany , pages 792 - 800, XP093078766, ISSN: 2193-5807, DOI: 10.1002/ajoc.201600095 *

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