GB539697A - Improvements in and relating to the manufacture of condensation products from trimethyl-hydroquinone - Google Patents
Improvements in and relating to the manufacture of condensation products from trimethyl-hydroquinoneInfo
- Publication number
- GB539697A GB539697A GB8708/39A GB870839A GB539697A GB 539697 A GB539697 A GB 539697A GB 8708/39 A GB8708/39 A GB 8708/39A GB 870839 A GB870839 A GB 870839A GB 539697 A GB539697 A GB 539697A
- Authority
- GB
- United Kingdom
- Prior art keywords
- trimethylhydroquinone
- bromide
- coumarane
- halogeno
- march
- 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
- 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
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
- C07D311/72—3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrane Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
539,697. Coumarane and chromane derivatives. HOFFMAN-LA ROCHE & CO. AKT.- GES., F. March 18, 1939, No. 8708. Convention date, March 18, 1938. Sample furnished. [Class 2 (iii)] Coumarane or chromane derivatives are obtained when the trimethylhydroquinone monoalkylene ethers obtained by the interaction of trimethylhydroquinone with halogenoalkylenes containing not more than six carbon atoms in the presence of acid-combining agents are first subjected to rearrangement by heating and the products then treated with acid condensing agents. The halogeno-alkylenes are of the formula hal.CH 2 .CH=CRR<SP>1</SP> ; if both Rand R<SP>1</SP> represent hydrogen a 2-methyl-5- oxycoumarane is obtained, but when both R & R<SP>1</SP> are alkyl, then a 2-alkyl-6-oxychromane results. The products are useful for the manufacture of therapeutic substances. According to the example, trimethylhydroquinone is heated with allyl bromide in the presence of anhydrous potassium carbonate and the resulting mono-allyl ether heated above 200‹ C. and then melted with pyridine hydrochloride, giving 2 : 4 : 6 : 7-tetramethyl-5-hydroxycoumarane. The sample furnished under Sect. 2 (5) consists of 2 : 2 : 5 : 7 : 8-pentamethyl-6- hydroxychromane and is prepared in a similar manner to the product of the example above, but using, instead of allyl bromide, the γγ- dimethylallyl bromide obtained by treating γγ-dimethylallyl alcohol with phosphorus tribromide. The Specification as open to inspection under Sect. 91 is not restricted to the use of halogeno-alkylenes containing not more than six carbon atoms and includes a further example describing the condensation of trimethylhydro-. quinone with phytyl bromide in the presence of anhydrous potassium carbonate, followed by the conversion of the resulting monophytyl ether with al-α-tocopherol, by first heating in decahydronaphthalene under reflux and then treating with anhydrous zinc chloride while stirring. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH539697X | 1938-03-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB539697A true GB539697A (en) | 1941-09-22 |
Family
ID=4518997
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8708/39A Expired GB539697A (en) | 1938-03-18 | 1939-03-18 | Improvements in and relating to the manufacture of condensation products from trimethyl-hydroquinone |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB539697A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2501896A (en) * | 1950-03-28 | Dichlorovinm ethers |
-
1939
- 1939-03-18 GB GB8708/39A patent/GB539697A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2501896A (en) * | 1950-03-28 | Dichlorovinm ethers |
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