GB921538A - Substituted benzoquinones and hydroquinones - Google Patents
Substituted benzoquinones and hydroquinonesInfo
- Publication number
- GB921538A GB921538A GB3333459A GB3333459A GB921538A GB 921538 A GB921538 A GB 921538A GB 3333459 A GB3333459 A GB 3333459A GB 3333459 A GB3333459 A GB 3333459A GB 921538 A GB921538 A GB 921538A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroquinone
- benzoquinone
- formula
- methyl
- compounds
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/26—Quinones containing groups having oxygen atoms singly bound to carbon atoms
- C07C50/28—Quinones containing groups having oxygen atoms singly bound to carbon atoms with monocyclic quinoid structure
-
- 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
- C07C46/00—Preparation of quinones
- C07C46/10—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises compounds of formulae:- <FORM:0921538/IV(a)/1> <FORM:0921538/IV(a)/2> wherein n is an integer from 1 to 5 and specifically the 2:3-dimethoxy-5-methyl-6-(31, 71-dimethyloctyl)- or -(31,71, 111-trimethyldodecyl)- or -(31-methylbutyl)- or -(31,71,111,151-tetramethylhexadecyl)- or -(31,71,111,151, 191-pentamethyleicosyl)-hydroquinones and benzoquinones. The compounds are prepared by reducing 2 : 3 - dimethoxy - 5 - methyl-benzoquinone to the corresponding hydroquinone using hydrogen and a palladium, platinum or Raney nickel catalyst or a reducing agent such as sulphur dioxide, sodium hydrosulphite, zinc and acetic acid or sodium borohydride. The hydroquinone is condensed with an alcohol of formula:- <FORM:0921538/IV(a)/3> such as geraniol and nerol (n = 2), farnesol (n = 3) and 3-methyl-2-buten-1-ol (n = 1), or of formula <FORM:0921538/IV(a)/4> such as phytol, or of formula <FORM:0921538/IV(a)/5> such as 3,7,11,15,19-pentamethyl-1-eicosen-3-ol, to yield a substituted hydroquinone of formula <FORM:0921538/IV(a)/6> or <FORM:0921538/IV(a)/7> Specified condensing agents are potassium acid sulphate, zinc chloride, oxalic acid, boron trifluoride and aluminium chloride. The reaction is carried out in an inert solvent such as dioxane, ether or dimethoxyethane and in an atmosphere of nitrogen. The hydroquinone is oxidised with a mild oxidising agent such as silver oxide, ferric chloride or air to the corresponding benzoquinone which is purified by chromatography from a solution in hexane. The benzoquinone is reduced catalytically in an inert solvent such as dioxane, ether, dimethoxyethane and hexane using hydrogen at an elevated pressure and palladium on charcoal, platinum, or Raney nickel as catalyst, to give the hydroquinone product. This may be oxidised to the benzoquinone product using the mild oxidising agents specified above. The preparation of the compounds specified above is described in examples.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US76503958A | 1958-10-03 | 1958-10-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB921538A true GB921538A (en) | 1963-03-20 |
Family
ID=25072471
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3333459A Expired GB921538A (en) | 1958-10-03 | 1959-10-01 | Substituted benzoquinones and hydroquinones |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE583084A (en) |
| GB (1) | GB921538A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2545511A1 (en) * | 1974-10-11 | 1976-04-22 | Eisai Co Ltd | PROCESS FOR THE PREPARATION OF 1,4-BENZOHYDROCHINONE DERIVATIVES |
| US3974187A (en) * | 1975-02-28 | 1976-08-10 | Wan Yieh Ping | Synthetic analogs having the activity of naturally occurring forms of coenzyme Q |
-
1959
- 1959-09-28 BE BE583084A patent/BE583084A/en unknown
- 1959-10-01 GB GB3333459A patent/GB921538A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2545511A1 (en) * | 1974-10-11 | 1976-04-22 | Eisai Co Ltd | PROCESS FOR THE PREPARATION OF 1,4-BENZOHYDROCHINONE DERIVATIVES |
| US3974187A (en) * | 1975-02-28 | 1976-08-10 | Wan Yieh Ping | Synthetic analogs having the activity of naturally occurring forms of coenzyme Q |
Also Published As
| Publication number | Publication date |
|---|---|
| BE583084A (en) | 1960-03-28 |
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