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GB1451317A - Preparation of phloroglucinol or its monomethyl ether - Google Patents

Preparation of phloroglucinol or its monomethyl ether

Info

Publication number
GB1451317A
GB1451317A GB5842172A GB5842172A GB1451317A GB 1451317 A GB1451317 A GB 1451317A GB 5842172 A GB5842172 A GB 5842172A GB 5842172 A GB5842172 A GB 5842172A GB 1451317 A GB1451317 A GB 1451317A
Authority
GB
United Kingdom
Prior art keywords
hydrogen atom
group
leaving group
leaving
dec
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
GB5842172A
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.)
Oce Andeno BV
Original Assignee
Oce Andeno BV
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 Oce Andeno BV filed Critical Oce Andeno BV
Priority to GB5842172A priority Critical patent/GB1451317A/en
Priority to JP48141136A priority patent/JPS5828259B2/en
Priority to US05/424,178 priority patent/US3959388A/en
Priority to IT7070673A priority patent/IT1000506B/en
Priority to NL7317137A priority patent/NL7317137A/xx
Priority to DE19732362694 priority patent/DE2362694C3/en
Priority to FR7345002A priority patent/FR2210597B1/fr
Priority to CA188,329A priority patent/CA1009256A/en
Publication of GB1451317A publication Critical patent/GB1451317A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
    • C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
    • C07C37/02—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis by substitution of halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1451317 Preparation of phloroglucinol or its monomethylether OCE-ANDENO BV 17 Dec 1973 [18 Dec 1972 10 Dec 1973] 58421/72 and 42494/73 Addition to 1388840 Heading C2C A process for the preparation of phloroglucinol or its monomethyl ether comprises: (i) reacting in an inert organic liquid medium which forms an azeotrope with water, a phenol of formula wherein R 1 and R 3 to R 5 , which may be the same or different, each represent a hydrogen atom or a leaving group (as hereinafter defined); and R 2 represents a hydrogen atom, a leaving group or a group of the formula -OR 6 , wherein R 6 represents a hydrogen atom or a methyl group, with the proviso that: (i) where R 2 represents a leaving group or a group of the formula -OR 6 , R 1 represents a hydrogen atom and only one of R 3 to R 5 represents a leaving group; and that (ii) where R 2 represents a hydrogen atom, two of R 1 , R 3 to R 5 represent leaving groups occupying positions such that, upon leaving, one yne bond can be formed at the 2,3 or the 3,4 position; and one yne bond can be formed at the 4,5 or the 5,6 position with an alkali metal hydroxide or a mixture thereof as a proton abstracting agent in the initial absence of water; (2) distilling off, as azeotrope, water produced by the reaction and (3) acidifying the alkali metal salt of the trihydroxybenzene or its monomethyl esther so formed to produce the corresponding compound with free hydroxyl groups. By 'leaving group' is meant any nucleophilic species weaker than -OH or -OCH 3 , e.g. a halogen atom. The reaction is preferably carried out at 130‹ to 180‹ C.
GB5842172A 1972-06-23 1972-12-18 Preparation of phloroglucinol or its monomethyl ether Expired GB1451317A (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
GB5842172A GB1451317A (en) 1972-12-18 1972-12-18 Preparation of phloroglucinol or its monomethyl ether
JP48141136A JPS5828259B2 (en) 1972-12-18 1973-12-10 Method for producing phloroglucin and its derivatives
US05/424,178 US3959388A (en) 1972-06-23 1973-12-12 Preparation of phloroglucinol or its monomethyl ether
IT7070673A IT1000506B (en) 1972-12-18 1973-12-14 PROCEDURE FOR THE PREPARATION OF FLOROGLUCINOL, ITS MONOMETHYL ETHER AND DIIDROXYBENZENES
NL7317137A NL7317137A (en) 1972-12-18 1973-12-14
DE19732362694 DE2362694C3 (en) 1972-12-18 1973-12-17 Process for the production of phloroglucinol or its monomethyl ether
FR7345002A FR2210597B1 (en) 1972-12-18 1973-12-17
CA188,329A CA1009256A (en) 1972-12-18 1973-12-17 Preparation of phloroglucinol and its monomethyl ether

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB5842172A GB1451317A (en) 1972-12-18 1972-12-18 Preparation of phloroglucinol or its monomethyl ether
GB4249473 1973-09-10

Publications (1)

Publication Number Publication Date
GB1451317A true GB1451317A (en) 1976-09-29

Family

ID=26264917

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5842172A Expired GB1451317A (en) 1972-06-23 1972-12-18 Preparation of phloroglucinol or its monomethyl ether

Country Status (7)

Country Link
JP (1) JPS5828259B2 (en)
CA (1) CA1009256A (en)
DE (1) DE2362694C3 (en)
FR (1) FR2210597B1 (en)
GB (1) GB1451317A (en)
IT (1) IT1000506B (en)
NL (1) NL7317137A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113480413A (en) * 2021-07-05 2021-10-08 四川海梦智森生物制药有限公司 Preparation method of phloroglucinol

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2840597A1 (en) * 1978-09-18 1980-03-27 Akzo Gmbh METHOD FOR PRODUCING PHLOROGLUCIN
US4319054A (en) * 1979-12-12 1982-03-09 Mitsubishi Chemical Industries Limited Process for producing pyrogallol
US4533765A (en) * 1983-12-07 1985-08-06 Air Products And Chemicals, Inc. Polyhydroxy aromatic compounds from alkali metal hydroxide and mononuclear aromatic compounds
US4533763A (en) * 1983-12-14 1985-08-06 Air Products And Chemicals, Inc. Hydroxy aromatic compounds from alkali metal hydroxide and mononuclear aromatic compound
CN115490573A (en) * 2022-09-27 2022-12-20 康普药业股份有限公司 Novel phloroglucinol synthesis process

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1907879C3 (en) * 1969-02-17 1978-11-02 Union Rheinische Braunkohlen Kraftstoff Ag, 5047 Wesseling Process for the preparation of alkyldihydroxybenzenes
DE2042569A1 (en) * 1970-08-27 1972-03-02 Biller, Efim, Freiburg (Schweiz) Phenol mixtures contg m-dioxybenzene prepn - by reacting o-or p-chlorophenol with alkali hydroxide under an hydrous conditions

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113480413A (en) * 2021-07-05 2021-10-08 四川海梦智森生物制药有限公司 Preparation method of phloroglucinol

Also Published As

Publication number Publication date
JPS5828259B2 (en) 1983-06-15
DE2362694B2 (en) 1979-11-15
JPS4994637A (en) 1974-09-09
FR2210597B1 (en) 1979-05-11
NL7317137A (en) 1974-06-20
CA1009256A (en) 1977-04-26
DE2362694C3 (en) 1980-07-24
FR2210597A1 (en) 1974-07-12
DE2362694A1 (en) 1974-06-20
IT1000506B (en) 1976-04-10

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee