GB786106A - Improvements in and relating to the production of phenols - Google Patents

Improvements in and relating to the production of phenols

Info

Publication number
GB786106A
GB786106A GB19503/55A GB1950355A GB786106A GB 786106 A GB786106 A GB 786106A GB 19503/55 A GB19503/55 A GB 19503/55A GB 1950355 A GB1950355 A GB 1950355A GB 786106 A GB786106 A GB 786106A
Authority
GB
United Kingdom
Prior art keywords
tert
alkyl
butyl
hydroxy
give
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
GB19503/55A
Inventor
Robert William Gunn Preston
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries 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
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB19503/55A priority Critical patent/GB786106A/en
Publication of GB786106A publication Critical patent/GB786106A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
    • C07C39/08—Dihydroxy benzenes; Alkylated derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C46/00—Preparation of quinones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C46/00—Preparation of quinones
    • C07C46/02—Preparation of quinones by oxidation giving rise to quinoid structures
    • C07C46/06—Preparation of quinones by oxidation giving rise to quinoid structures of at least one hydroxy group on a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C50/00—Quinones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C50/00—Quinones
    • C07C50/02—Quinones with monocyclic quinoid structure

Landscapes

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

Abstract

Phenols of formula <FORM:0786106/IV (a)/1> wherein X and Y are tertiary alkyl groups and R is an alkyl or substituted alkyl group (e.g. benzyl), are prepared by reacting a 3:5-di-tert.-alkyl-4-hydroxy-benzaldehyde with hydrogen peroxide, in the presence of an aqueous solution of an alkali metal hydroxide and a gas containing free oxygen to give a 2:6-di-tert.-alkyl-parabenzoquinone, reducing this to the corresponding hydroquinone and finally alkylating the hydroquinone. The molar ratio of hydrogen peroxide to hydroxy aldehyde is preferably at least 1:1 and the aqueous alkali metal hydroxide solution is preferably in a stoichiometric excess over the hydroxy-aldehyde. The reduction may be effected catalytically using a copper catalyst or with reagents which liberate nascent hydrogen such as zinc and an acid. The alkylation is carried out in known manner using, for example, an alkyl halide or dialkyl sulphate. In an example, air was blown into a mixture of hydrogen peroxide, 3:5 - di - tert. - butyl - 4 - hydroxy-benzaldehyde and aqueous sodium hydroxide to give 2:6-di-tert.-butyl-parabenzoquinone which was reduced with zinc and acetic acid to 2:6-di-tert.-butyl-hydroquinone which was alkylated with dimethyl sulphate to give 2:6-di-tert.-butyl-4-methoxy-phenol.
GB19503/55A 1955-07-06 1955-07-06 Improvements in and relating to the production of phenols Expired GB786106A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB19503/55A GB786106A (en) 1955-07-06 1955-07-06 Improvements in and relating to the production of phenols

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB19503/55A GB786106A (en) 1955-07-06 1955-07-06 Improvements in and relating to the production of phenols

Publications (1)

Publication Number Publication Date
GB786106A true GB786106A (en) 1957-11-13

Family

ID=10130440

Family Applications (1)

Application Number Title Priority Date Filing Date
GB19503/55A Expired GB786106A (en) 1955-07-06 1955-07-06 Improvements in and relating to the production of phenols

Country Status (1)

Country Link
GB (1) GB786106A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4482756A (en) * 1982-04-29 1984-11-13 Sun Tech, Inc. Production of hydroquinones

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4482756A (en) * 1982-04-29 1984-11-13 Sun Tech, Inc. Production of hydroquinones

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