FR2317263A1 - Pyrogallol prodn. from (di) halo phenol (ethers) - by reaction with alkoxide to di- or tri ether, then dealkylation (NL301276) - Google Patents

Pyrogallol prodn. from (di) halo phenol (ethers) - by reaction with alkoxide to di- or tri ether, then dealkylation (NL301276)

Info

Publication number
FR2317263A1
FR2317263A1 FR7619528A FR7619528A FR2317263A1 FR 2317263 A1 FR2317263 A1 FR 2317263A1 FR 7619528 A FR7619528 A FR 7619528A FR 7619528 A FR7619528 A FR 7619528A FR 2317263 A1 FR2317263 A1 FR 2317263A1
Authority
FR
France
Prior art keywords
dealkylation
salts
alkyl
pyrogallol
alkoxide
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.)
Granted
Application number
FR7619528A
Other languages
French (fr)
Other versions
FR2317263B1 (en
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.)
Fisons Ltd
Original Assignee
Fisons Ltd
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
Priority claimed from GB27430/75A external-priority patent/GB1549858A/en
Application filed by Fisons Ltd filed Critical Fisons Ltd
Publication of FR2317263A1 publication Critical patent/FR2317263A1/en
Application granted granted Critical
Publication of FR2317263B1 publication Critical patent/FR2317263B1/fr
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
    • C07C65/03—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring
    • 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
    • C07C37/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • 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
    • C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups

Landscapes

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

Abstract

The prepn. of pyrogallol (I), or its salts, comprises reacting halo cpds. (II), or their salts, with an alkoxide ROM to give the ether (III), or its salts, which is then subjected to dealkylation and elimination of R1 = H. A and C = Br or I; and B = OR2; or one of A and B = Br or I, the other and C = OR2. A1 and C1 = R and B1 = R2, or one of A1 and B1 = R, the other and C1 = R2. R= 1-4C alkyl. R1 = H, 10C sec. or tert. alkyl, COOH or 2-5C alkoxycarbonyl. R2 = H or 1-4C alkyl. M = alkali metal. (I) is used as photographic developer, in dyeing of wool and leather; in analysis of heavy metals and as an intermediate, e.g., for the insecticide 2,2-dimethyl-1,3-benzodioxol-4-yl methyl carbamate. The process gives high yields of pure prod. without relying on scare starting matls. of vegetable origin. Pref. first stage is in presence of a Cu salt catalyst and dealkylation and R1 removal is done with aq. HBr. 2,6-dibromo-4-t.-butylphenol was converted in 77% yield to the 2,6-dimethoxy cpd. with Na methoxide and CuI, and this refluxed with 48% HBr to give an 83% yield of (I).
FR7619528A 1975-06-28 1976-06-25 Pyrogallol prodn. from (di) halo phenol (ethers) - by reaction with alkoxide to di- or tri ether, then dealkylation (NL301276) Granted FR2317263A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB27430/75A GB1549858A (en) 1975-06-28 1975-06-28 Production of pyrogallol
GB280176 1976-01-24

Publications (2)

Publication Number Publication Date
FR2317263A1 true FR2317263A1 (en) 1977-02-04
FR2317263B1 FR2317263B1 (en) 1982-10-22

Family

ID=26237738

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7619528A Granted FR2317263A1 (en) 1975-06-28 1976-06-25 Pyrogallol prodn. from (di) halo phenol (ethers) - by reaction with alkoxide to di- or tri ether, then dealkylation (NL301276)

Country Status (5)

Country Link
JP (1) JPS6039057B2 (en)
DE (1) DE2627874A1 (en)
FR (1) FR2317263A1 (en)
IL (1) IL49803A (en)
NL (1) NL7606835A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0025659A2 (en) * 1979-09-14 1981-03-25 Fbc Limited Processes for the production of 1,2,3-trihydroxyphenyl compounds

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5553229A (en) * 1978-10-13 1980-04-18 Otsuka Chem Co Ltd Preparation of alkoxyphenol compound
GB2097000B (en) * 1979-03-19 1983-11-30 Riker Laboratories Inc Process for the preparation of 1,4-bis(2,2,2-trifluoroethoxy) benzene
JP3364727B2 (en) * 1993-10-22 2003-01-08 イハラケミカル工業株式会社 2,2-bis (3,5-disubstituted-4-hydroxyphenyl) propane derivative, method for producing the same, and method for producing pyrogallol using the derivative
DE4423356A1 (en) 1994-07-04 1996-01-11 Bayer Ag Improved process for the preparation of 3,5-dihydroxy-4-bromobenzoic acid
JP2009001506A (en) * 2007-06-19 2009-01-08 Sankyo Kasei Kk Production method of trihydroxybenzophenone

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE493198C (en) * 1927-10-04 1930-03-05 Holzverkohlungs Ind Akt Ges Process for the production of polyhydric phenols and their homologues from wood tar and wood tar oil with simultaneous production of methanol

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1942827A (en) * 1933-03-27 1934-01-09 Dow Chemical Co Tertiary alkyl substituted orthodihydroxy benzenes
DE2210254A1 (en) * 1972-03-03 1973-09-06 Dynamit Nobel Ag METHOD FOR MANUFACTURING PHENOLAETHERS OR PHENOLS
NL179047C (en) * 1973-12-11 1986-07-01 Oce Andeno Bv PROCESS FOR THE PREPARATION OF S-TRIMETHOXY-BENZENE.

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE493198C (en) * 1927-10-04 1930-03-05 Holzverkohlungs Ind Akt Ges Process for the production of polyhydric phenols and their homologues from wood tar and wood tar oil with simultaneous production of methanol

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
EXBK/41 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0025659A2 (en) * 1979-09-14 1981-03-25 Fbc Limited Processes for the production of 1,2,3-trihydroxyphenyl compounds
EP0025659A3 (en) * 1979-09-14 1981-07-22 Fbc Limited Processes for the production of 1,2,3-trihydroxyphenyl compounds; processes for the production of substituted phenol compounds and of derivatives thereof; 2,6-dimethyl phenol derivatives

Also Published As

Publication number Publication date
JPS6039057B2 (en) 1985-09-04
IL49803A (en) 1979-11-30
NL7606835A (en) 1976-12-30
DE2627874C2 (en) 1987-12-03
JPS525721A (en) 1977-01-17
IL49803A0 (en) 1976-08-31
FR2317263B1 (en) 1982-10-22
DE2627874A1 (en) 1977-01-13

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Legal Events

Date Code Title Description
ST Notification of lapse